WO2020035599A1 - Novel compositions, their use, and methods for their formation - Google Patents
Novel compositions, their use, and methods for their formation Download PDFInfo
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- WO2020035599A1 WO2020035599A1 PCT/EP2019/072026 EP2019072026W WO2020035599A1 WO 2020035599 A1 WO2020035599 A1 WO 2020035599A1 EP 2019072026 W EP2019072026 W EP 2019072026W WO 2020035599 A1 WO2020035599 A1 WO 2020035599A1
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- oligosaccharides
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/262—Cellulose; Derivatives thereof, e.g. ethers
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
- A23L33/24—Cellulose or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H8/00—Macromolecular compounds derived from lignocellulosic materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/14—Hemicellulose; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/12—Disaccharides
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/32—Foods, ingredients or supplements having a functional effect on health having an effect on the health of the digestive tract
- A23V2200/3202—Prebiotics, ingredients fermented in the gastrointestinal tract by beneficial microflora
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/28—Oligosaccharides
- A23V2250/284—Oligosaccharides, non digestible
Definitions
- Dietary fibre is an important part of a positive diet and helps maintain digestive health and a well-regulated gut flora.
- Such fibre comprises saccharides of varying chain lengths and types.
- fibre can also be produced separately and added to other foods during their manufacture.
- compositions comprising a mixture of oligosaccharides that surprisingly have improved and tunable properties that make them useful as ingredients in foodstuffs, cosmetics, and nutraceuticals, particularly as sugar substitutes.
- described herein are economical and efficient methods of preparing or manufacturing sugar substitutes comprising one or more oligosaccharides and one or more polysaccharides using enzymatic processes. These processes can be used to create different formulations comprising different types and amounts of the one or more oligosaccharides and the one or more polysaccharides to produce the desired properties.
- a consumable composition may comprise cello-oligosaccharides with a degree of polymerization of from two to six.
- the composition may also comprise at least one more type of oligosaccharide selected from: xylo-oligosaccharides with a degree of polymerization of from two to twelve, mixed-linkage glucan oligosaccharides with a degree of polymerization of from two to five or manno-oligosaccharides having a degree of polymerization of from two to twelve, xyloglucan oligosaccharides having a degree of polymerization of from four to twelve.
- the cello- oligosaccharide and the one more type of oligosaccharide can form at least 50% of the consumable composition w/w.
- the one more type of oligosaccharide may be xylo- oligosaccharides with a degree of polymerization of from two to twelve.
- the one more type of oligosaccharide may be mixed-linkage glucan oligosaccharides with a degree of polymerization of from two to five.
- the one more type of oligosaccharide may be manno- oligosaccharides having a degree of polymerization of from two to twelve.
- the one more type of oligosaccharide may be xyloglucan oligosaccharides having a degree of polymerization of from four to twelve.
- compositions further comprise polysaccharides.
- the source of the polysaccharides may be a biomass.
- the biomass comprises com stover, com cob, wheat bran, wheat straw, hardwood, softwood, cellulose, chitin, chitosan, xylan, xyloglucan, mixed-linkage glucan, mannan, lignocellulose, or a combination thereof.
- the composition comprises at least 5% cello-oligosaccharides with a degree of polymerization of from two to six w/w.
- the composition comprises at most 90% cello-oligosaccharides with a degree of polymerization of from two to six w/w.
- the composition comprises at most 50% cello-oligosaccharides with a degree of polymerization of from two to six w/w.
- the consumable composition comprises at least 5% polysaccharides w/w.
- the consumable composition comprises at most 50% polysaccharides w/w.
- the cello-oligosaccharides are a mixture comprising cello- oligosaccharides with a degree of polymerization of two, three, four, five, six, or a combination thereof.
- the cello-oligosaccharide mixture comprises at least 5% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 15% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 30% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 50% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 80% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 90% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 5% of cello- oligosaccharides with a degree of polymerization of three w/w.
- the cello-oligosaccharide mixture comprises at least 5% of cello- oligosaccharides with a degree of polymerization of four w/w.
- the cello-oligosaccharide mixture comprises at least 5% of cello- oligosaccharides with a degree of polymerization of five w/w.
- the cello-oligosaccharide mixture comprises at least 5% of cello- oligosaccharides with a degree of polymerization of six w/w.
- the cello-oligosaccharide mixture comprises at most 20% of cello- oligosaccharides with a degree of polymerization of three w/w.
- the cello-oligosaccharide mixture comprises at most 15% of cello- oligosaccharides with a degree of polymerization of four w/w.
- the cello-oligosaccharide mixture comprises at most 10% of cello- oligosaccharides with a degree of polymerization of five w/w.
- the cello-oligosaccharide mixture comprises at most 8% of cello- oligosaccharides with a degree of polymerization of six w/w.
- the xylo-oligosaccharides are a mixture comprising xylo- oligosaccharides with a degree of polymerization of two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, or a combination thereof.
- the composition comprises at least 5% xylo-oligosaccharides with a degree of polymerization of from two to twelve w/w.
- the xylo-oligosaccharide mixture comprises at least 4% of xylo- oligosaccharides with a degree of polymerization of two w/w.
- the xylo-oligosaccharide mixture comprises at least 15% of xylo- oligosaccharides with a degree of polymerization of two w/w.
- the xylo-oligosaccharide mixture comprises at least 30% of xylo- oligosaccharides with a degree of polymerization of two w/w.
- the xylo-oligosaccharide mixture comprises at least 50% of xylo- oligosaccharides with a degree of polymerization of two w/w.
- the xylo-oligosaccharide mixture comprises at least 70% of xylo- oligosaccharides with a degree of polymerization of two w/w.
- the xylo-oligosaccharide mixture comprises at least 5% of xylo- oligosaccharides with a degree of polymerization of three w/w.
- the xylo-oligosaccharide mixture comprises at least 8% of xylo- oligosaccharides with a degree of polymerization of three w/w.
- the xylo-oligosaccharide mixture comprises at least 15% of xylo- oligosaccharides with a degree of polymerization of three w/w.
- the xylo-oligosaccharide mixture comprises at least 5% of xylo- oligosaccharides with a degree of polymerization of four w/w.
- the xylo-oligosaccharide mixture comprises at least 5% of xylo- oligosaccharides with a degree of polymerization of five w/w.
- the xylo-oligosaccharide mixture comprises at least 10% of xylo- oligosaccharides with a degree of polymerization of six w/w.
- the xylo-oligosaccharide mixture comprises at least 3% of xylo- oligosaccharides with a degree of polymerization of seven w/w.
- the xylo-oligosaccharide mixture comprises at least 4% of xylo- oligosaccharides with a degree of polymerization of eight w/w.
- the xylo-oligosaccharide mixture comprises at least 2% of xylo- oligosaccharides with a degree of polymerization of nine w/w.
- the xylo-oligosaccharide mixture comprises at least 1% of xylo- oligosaccharides with a degree of polymerization of ten w/w.
- the xylo-oligosaccharide mixture comprises at least 1% of xylo- oligosaccharides with a degree of polymerization of eleven w/w. [0050] In some embodiments, the xylo-oligosaccharide mixture comprises at most 15% of xylo- oligosaccharides with a degree of polymerization of four w/w.
- the xylo-oligosaccharide mixture comprises at most 15% of xylo- oligosaccharides with a degree of polymerization of five w/w.
- the xylo-oligosaccharide mixture comprises at most 20% of xylo- oligosaccharides with a degree of polymerization of six w/w.
- the xylo-oligosaccharide mixture comprises at most 15% of xylo- oligosaccharides with a degree of polymerization of seven w/w.
- the xylo-oligosaccharide mixture comprises at most 20% of xylo- oligosaccharides with a degree of polymerization of eight w/w.
- the xylo-oligosaccharide mixture comprises at most 10% of xylo- oligosaccharides with a degree of polymerization of nine w/w.
- the xylo-oligosaccharide mixture comprises at most 5% of xylo- oligosaccharides with a degree of polymerization of ten w/w.
- the xylo-oligosaccharide mixture comprises at most 5% of xylo- oligosaccharides with a degree of polymerization of eleven w/w.
- the manno-oligosaccharides are a mixture comprising manno- oligosaccharides with a degree of polymerization of two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, or a combination thereof.
- the manno-oligosaccharide mixture comprises at least 4% of manno-oligosaccharides with a degree of polymerization of two w/w.
- the manno-oligosaccharide mixture comprises at least 15% of manno-oligosaccharides with a degree of polymerization of two w/w.
- the manno-oligosaccharide mixture comprises at least 30% of manno-oligosaccharides with a degree of polymerization of two w/w.
- the manno-oligosaccharide mixture comprises at least 50% of manno-oligosaccharides with a degree of polymerization of two w/w.
- the manno-oligosaccharide mixture comprises at least 70% of manno-oligosaccharides with a degree of polymerization of two w/w.
- the manno-oligosaccharide mixture comprises at least 5% of manno-oligosaccharides with a degree of polymerization of three w/w.
- the manno-oligosaccharide mixture comprises at least 8% of manno-oligosaccharides with a degree of polymerization of three w/w. [0066] In some embodiments, the manno-oligosaccharide mixture comprises at least 15% of manno-oligosaccharides with a degree of polymerization of three w/w.
- the manno-oligosaccharide mixture comprises at least 5% of manno-oligosaccharides with a degree of polymerization of four w/w.
- the manno-oligosaccharide mixture comprises at least 5% of manno-oligosaccharides with a degree of polymerization of five w/w.
- the manno-oligosaccharide mixture comprises at least 10% of manno-oligosaccharides with a degree of polymerization of six w/w.
- the manno-oligosaccharide mixture comprises at least 3% of manno-oligosaccharides with a degree of polymerization of seven w/w.
- the manno-oligosaccharide mixture comprises at least 4% of manno-oligosaccharides with a degree of polymerization of eight w/w.
- the manno-oligosaccharide mixture comprises at least 2% of manno-oligosaccharides with a degree of polymerization of nine w/w.
- the manno-oligosaccharide mixture comprises at least 1% of manno-oligosaccharides with a degree of polymerization of ten w/w.
- the manno-oligosaccharide mixture comprises at least 1% of manno-oligosaccharides with a degree of polymerization of eleven w/w.
- the manno-oligosaccharide mixture comprises at most 15% of manno-oligosaccharides with a degree of polymerization of four w/w.
- the manno-oligosaccharide mixture comprises at most 15% of manno-oligosaccharides with a degree of polymerization of five w/w.
- the manno-oligosaccharide mixture comprises at most 20% of manno-oligosaccharides with a degree of polymerization of six w/w.
- the manno-oligosaccharide mixture comprises at most 15% of manno-oligosaccharides with a degree of polymerization of seven w/w.
- the manno-oligosaccharide mixture comprises at most 20% of manno-oligosaccharides with a degree of polymerization of eight w/w.
- the manno-oligosaccharide mixture comprises at most 10% of manno-oligosaccharides with a degree of polymerization of nine w/w.
- the manno-oligosaccharide mixture comprises at most 5% of manno-oligosaccharides with a degree of polymerization of ten w/w.
- the manno-oligosaccharide mixture comprises at most 5% of manno-oligosaccharides with a degree of polymerization of eleven w/w.
- the composition comprises at least 5% mixed-linkage glucan oligosaccharides with a degree of polymerization of from two to five w/w.
- the consumable composition may be used as an ingredient in a finished product.
- the concentration of the consumable composition in the ingredient may be at least 20% w/w.
- the concentration of the consumable composition in the ingredient may be at least 40% w/w.
- the concentration of the consumable composition in the ingredient may be at least 60% w/w.
- the finished product may be a foodstuff.
- the finished product may be a cosmetic.
- the finished product may be a nutraceutical.
- the concentration of the consumable composition in the finished product may be at least 1% w/w.
- the concentration of the consumable composition in the finished product may be at least 2% w/w.
- the concentration of the consumable composition in the finished product may be at least 5% w/w.
- the concentration of the consumable composition in the finished product may be at least 10% w/w.
- composition may comprise less than 5% monosaccharides w/w.
- the composition may be used as a sweetener composition.
- the sweetness of the compositions may be comparable to a control composition, wherein the control composition comprises primarily monosaccharides, disaccharides or a combination thereof.
- the sweetness of the compositions may be higher than the sweetness of a control composition, wherein the control composition comprises primarily monosaccharides, disaccharides or a combination thereof.
- the composition may be used as a binding composition.
- the binding properties of the composition are comparable to a control composition, wherein the control composition comprises primarily monosaccharides, disaccharides or a combination thereof.
- the binding properties of the compositions are higher than the binding properties of a control composition, wherein the control composition comprises primarily monosaccharides, disaccharides or a combination thereof.
- the composition may be used as a fibre content enhancer.
- the fibre content of the compositions may be comparable to a control composition, wherein the control composition comprises primarily monosaccharides, disaccharides or a combination thereof.
- the fibre content of the compositions may be higher than the fibre content of a control composition, wherein the control composition comprises primarily monosaccharides, disaccharides or a combination thereof.
- the gastro-intestinal tolerance of the composition may be comparable or higher than the gastro-intestinal tolerance of a control composition, wherein the control composition comprises primarily monosaccharides, disaccharides or a combination thereof.
- the gastro-intestinal tolerance of the composition may be comparable or higher than the gastro-intestinal tolerance of a control composition, wherein the control composition comprises primarily one type of oligosaccharide.
- a consumable composition may comprise xylo-oligosaccharides with a degree of polymerization of from two to twelve.
- the composition may further comprise at least one more type of oligosaccharide selected from: cello- oligosaccharides with a degree of polymerization of from two to six, mixed-linkage glucan oligosaccharides with a degree of polymerization of from two to five, manno-oligosaccharides having a degree of polymerization of from two to twelve or xyloglucan oligosaccharides having a degree of polymerization of from four to twelve.
- the xylo-oligosaccharide and the one more type of oligosaccharide may form at least 50% of the consumable composition w/w.
- the one more type of oligosaccharide may be cello- oligosaccharides with a degree of polymerization of from two to six.
- the one more type of oligosaccharide may be mixed-linkage glucan oligosaccharides with a degree of polymerization of from two to five.
- the one more type of oligosaccharide may be manno- oligosaccharides having a degree of polymerization of from two to twelve.
- the one more type of oligosaccharide may be xyloglucan oligosaccharides having a degree of polymerization of from four to twelve.
- the composition further comprises polysaccharides.
- the source of the polysaccharides may be a biomass.
- the biomass comprises com stover, com cob, wheat bran, wheat straw, hardwood, softwood, cellulose, chitin, chitosan, xylan, xyloglucan, mixed-linkage glucan, mannan, lignocellulose, or a combination thereof.
- the composition comprises at least 5% cello-oligosaccharides with a degree of polymerization of from two to six w/w.
- the composition comprises at most 90% cello-oligosaccharides with a degree of polymerization of from two to six w/w.
- the composition comprises at most 50% cello-oligosaccharides with a degree of polymerization of from two to six w/w.
- the consumable composition comprises at least 5% polysaccharides w/w.
- the consumable composition comprises at most 50% polysaccharides w/w.
- the cello-oligosaccharides are a mixture comprising cello- oligosaccharides with a degree of polymerization of two, three, four, five, six, or a combination thereof.
- the cello-oligosaccharide mixture comprises at least 5% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 15% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 30% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 50% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 80% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 90% of cello- oligosaccharides with a degree of polymerization of two w/w.
- the cello-oligosaccharide mixture comprises at least 5% of cello- oligosaccharides with a degree of polymerization of three w/w.
- the cello-oligosaccharide mixture comprises at least 5% of cello- oligosaccharides with a degree of polymerization of four w/w. [0129] In some embodiments, the cello-oligosaccharide mixture comprises at least 5% of cello- oligosaccharides with a degree of polymerization of five w/w.
- the cello-oligosaccharide mixture comprises at least 5% of cello- oligosaccharides with a degree of polymerization of six w/w.
- the cello-oligosaccharide mixture comprises at most 20% of cello- oligosaccharides with a degree of polymerization of three w/w.
- the cello-oligosaccharide mixture comprises at most 15% of cello- oligosaccharides with a degree of polymerization of four w/w.
- the cello-oligosaccharide mixture comprises at most 10% of cello- oligosaccharides with a degree of polymerization of five w/w.
- the cello-oligosaccharide mixture comprises at most 8% of cello- oligosaccharides with a degree of polymerization of six w/w.
- the xylo-oligosaccharides are a mixture comprising xylo- oligosaccharides with a degree of polymerization of two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, or a combination thereof.
- the composition comprises at least 5% xylo-oligosaccharides with a degree of polymerization of from two to twelve w/w.
- the xylo-oligosaccharide mixture comprises at least 4% of xylo- oligosaccharides with a degree of polymerization of two w/w.
- the xylo-oligosaccharide mixture comprises at least 15% of xylo- oligosaccharides with a degree of polymerization of two w/w.
- the xylo-oligosaccharide mixture comprises at least 30% of xylo- oligosaccharides with a degree of polymerization of two w/w.
- the xylo-oligosaccharide mixture comprises at least 50% of xylo- oligosaccharides with a degree of polymerization of two w/w.
- the xylo-oligosaccharide mixture comprises at least 70% of xylo- oligosaccharides with a degree of polymerization of two w/w.
- the xylo-oligosaccharide mixture comprises at least 5% of xylo- oligosaccharides with a degree of polymerization of three w/w.
- the xylo-oligosaccharide mixture comprises at least 8% of xylo- oligosaccharides with a degree of polymerization of three w/w.
- the xylo-oligosaccharide mixture comprises at least 15% of xylo- oligosaccharides with a degree of polymerization of three w/w. [0145] In some embodiments, the xylo-oligosaccharide mixture comprises at least 5% of xylo- oligosaccharides with a degree of polymerization of four w/w.
- the xylo-oligosaccharide mixture comprises at least 5% of xylo- oligosaccharides with a degree of polymerization of five w/w.
- the xylo-oligosaccharide mixture comprises at least 10% of xylo- oligosaccharides with a degree of polymerization of six w/w.
- the xylo-oligosaccharide mixture comprises at least 3% of xylo- oligosaccharides with a degree of polymerization of seven w/w.
- the xylo-oligosaccharide mixture comprises at least 4% of xylo- oligosaccharides with a degree of polymerization of eight w/w.
- the xylo-oligosaccharide mixture comprises at least 2% of xylo- oligosaccharides with a degree of polymerization of nine w/w.
- the xylo-oligosaccharide mixture comprises at least 1% of xylo- oligosaccharides with a degree of polymerization of ten w/w.
- the xylo-oligosaccharide mixture comprises at least 1% of xylo- oligosaccharides with a degree of polymerization of eleven w/w.
- the xylo-oligosaccharide mixture comprises at most 15% of xylo- oligosaccharides with a degree of polymerization of four w/w.
- the xylo-oligosaccharide mixture comprises at most 15% of xylo- oligosaccharides with a degree of polymerization of five w/w.
- the xylo-oligosaccharide mixture comprises at most 20% of xylo- oligosaccharides with a degree of polymerization of six w/w.
- the xylo-oligosaccharide mixture comprises at most 15% of xylo- oligosaccharides with a degree of polymerization of seven w/w.
- the xylo-oligosaccharide mixture comprises at most 20% of xylo- oligosaccharides with a degree of polymerization of eight w/w.
- the xylo-oligosaccharide mixture comprises at most 10% of xylo- oligosaccharides with a degree of polymerization of nine w/w.
- the xylo-oligosaccharide mixture comprises at most 5% of xylo- oligosaccharides with a degree of polymerization of ten w/w.
- the xylo-oligosaccharide mixture comprises at most 5% of xylo- oligosaccharides with a degree of polymerization of eleven w/w.
- the manno-oligosaccharides are a mixture comprising manno- oligosaccharides with a degree of polymerization of two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, or a combination thereof
- the composition comprises at least 5% mixed-linkage glucan oligosaccharides with a degree of polymerization of from two to five w/w.
- the consumable composition may be used as an ingredient in a finished product.
- the concentration of the consumable composition in the ingredient may be at least 20% w/w.
- the concentration of the consumable composition in the ingredient may be at least 40% w/w.
- the concentration of the consumable composition in the ingredient may be at least 60% w/w.
- the finished product may be a foodstuff.
- the finished product may be a cosmetic.
- the finished product may be a nutraceutical.
- the concentration of the consumable composition in the finished product may be at least 1% w/w.
- the concentration of the consumable composition in the finished product may be at least 2% w/w.
- the concentration of the consumable composition in the finished product may be at least 5% w/w.
- the concentration of the consumable composition in the finished product may be at least 10% w/w.
- the composition comprises less than 5% monosaccharides w/w.
- the composition may be used as a sweetener composition.
- the sweetness of the compositions may be comparable to a control composition, wherein the control composition comprises primarily monosaccharides, disaccharides or a combination thereof.
- the sweetness of the compositions may be higher than the sweetness of a control composition, wherein the control composition comprises primarily monosaccharides, disaccharides or a combination thereof.
- the gastro-intestinal tolerance of the composition may be comparable or higher than the gastro-intestinal tolerance of a control composition, wherein the control composition comprises primarily monosaccharides, disaccharides or a combination thereof.
- the gastro-intestinal tolerance of the composition may be comparable or higher than the gastro-intestinal tolerance of a control composition, wherein the control composition comprises primarily one type of oligosaccharide.
- a foodstuff ingredient, cosmetic ingredient, or nutraceutical ingredient composition comprising at least two oligosaccharides.
- the oligosaccharides may be selected from the list consisting of cello-oligosaccharides having a degree of polymerisation of from two to six, xylo-oligosaccharides having a degree of polymerisation of from two to twelve, mixed-linkage glucan oligosaccharides having a degree of polymerisation of from two to five, manno-oligosaccharides having a degree of polymerisation of from two to twelve, xyloglucan oligosaccharides having a degree of polymerisation of from four to twelve, and chito-oligosaccharides having a degree of polymerisation of from two to twelve.
- the composition may comprise at least 10% by dry weight of each of the at least two oligosaccharides; wherein the ingredient comprises at least 50% by dry weight of saccharide present.
- the composition comprises at least 20% by dry weight, preferably at least 30% by dry weight, cello-oligosaccharides having a degree of polymerisation of from two to six.
- the composition comprises at least 20% by dry weight, preferably at least 30% by dry weight, xylo-oligosaccharides having a degree of polymerisation of from two to twelve.
- the composition comprises at least 20% by dry weight, preferably at least 30% by dry weight, mixed-linkage glucan oligosaccharides having a degree of polymerisation of from two to five.
- the composition comprises at least 20% by dry weight, preferably at least 30% by dry weight, manno-oligosaccharides having a degree of polymerisation of from two to twelve.
- the composition comprises at least 20% by dry weight, preferably at least 30% by dry weight, xyloglucan oligosaccharides having a degree of polymerisation of from four to twelve.
- the composition comprises at least 20% by dry weight, preferably at least 30% by dry weight, chito-oligosaccharides having a degree of polymerisation of from two to twelve.
- the composition comprises a polysaccharide, preferably a cellulosic polysaccharide, such as cellulose, or a polysaccharide derivative, preferably a cellulose derivative, such as carboxymethylcellulose, or a polysaccharide aggregate, such as lignocellulosic material, preferably undigested lignocellulosic material, such as from an enzymatic reaction that produced the oligosaccharides, preferably the composition comprises from greater than 0 to 40% by dry weight of the polysaccharide, the polysaccharide derivative or the polysaccharide aggregate.
- the composition comprises a phenolic compound, preferably a portion of lignin or a product of lignin breakdown.
- the composition may be in dry form.
- a foodstuff, cosmetic, or nutraceutical comprising an oligosaccharide mixture, wherein the oligosaccharide mixture comprises two oligosaccharides.
- the oligosaccharides may be selected from the list consisting of cello-oligosaccharides having a degree of polymerisation of from two to six, xylo-oligosaccharides having a degree of polymerisation of from two to twelve, mixed-linkage glucan oligosaccharides having a degree of polymerisation of from two to five, manno-oligosaccharides having a degree of polymerisation of from two to twelve, xyloglucan oligosaccharides having a degree of polymerisation of from four to twelve; and chito-oligosaccharides having a degree of polymerisation of from two to twelve.
- the two oligosaccharides may be present in a ratio of from 1 :9 to 9: 1 , preferably from 1 :4 to 4: 1 , more preferably from 1 :3 to 3:1, most preferably 2:3 to 3:2, in relation to each other, optionally wherein the oligosaccharide mixture comprises third oligosaccharides selected from the list.
- the ingredient may comprise at least 50% by dry weight of the two oligosaccharides present.
- a foodstuff ingredient, cosmetic ingredient, or nutraceutical ingredient composition comprising a saccharide component.
- the saccharide component may comprise monosaccharides at ⁇ 5% w/w of total saccharide component (comprising glucose, xylose and/or mannose), disaccharides at >20% w/w of total saccharide component (comprising cello-, xylo- and/or manno-oligosaccharides), wherein the disaccharides are at ⁇ 50% w/w of total saccharide component, trisaccharides at >5% w/w of total saccharide component (comprising cello-, xylo- and/or manno-oligosaccharides), tetrasaccharides at >2% w/w of total saccharide component (comprising cello-, xylo- and/or manno-oligosaccharides).
- the total composition may comprise at
- the foodstuff ingredient, cosmetic ingredient, or nutraceutical ingredient composition comprises less than 4% by dry weight of total saccharide component, preferably less than 3% by dry weight of total saccharide component, monosaccharides (comprising glucose, xylose and/or mannose).
- the composition comprises at least 25% by dry weight of total saccharide component, preferably at least 30% by dry weight of total saccharide component, disaccharides (comprising cello-, xylo- and/or manno-oligosaccharides).
- composition comprises at least 7.5% by dry weight of total saccharide component, preferably at least 10% by dry weight of total saccharide component, trisaccharides (comprising cello-, xylo- and/or manno-oligosaccharides).
- the composition comprises at least 3% by dry weight of total saccharide component, preferably at least 4% by dry weight of total saccharide component, tetrasaccharides (comprising cello-, xylo- and/or manno-oligosaccharides).
- the composition comprises at least 30%, preferably at least 40%, more preferably at least 50%, by dry weight saccharides.
- the composition comprises a polysaccharide, preferably a cellulosic polysaccharide, such as cellulose, or a hemicellulosic polysaccharide, such as xylan, or a polysaccharide derivative, preferably a cellulose derivative, such as carboxymethylcellulose, or a polysaccharide aggregate, such as lignocellulosic material, preferably undigested lignocellulosic material, such as from an enzymatic reaction that produced the oligosaccharides, preferably the composition comprises from greater than 0 to 40% by dry weight of the polysaccharide, the polysaccharide derivative or the polysaccharide aggregate.
- a polysaccharide preferably a cellulosic polysaccharide, such as cellulose, or a hemicellulosic polysaccharide, such as xylan
- a polysaccharide derivative preferably a cellulose derivative, such as carboxymethylcellulose
- the composition comprises a phenolic compound, preferably a portion of lignin or a product of lignin breakdown.
- a foodstuff ingredient, cosmetic ingredient, or nutraceutical ingredient comprising at least two oligosaccharides derived from lignocellulosic polymers.
- the oligosaccharides may be selected from the list consisting of cellulose, xylan, mixed-linkage glucan, mannan, xyloglucan, chitin, or a combination thereof.
- the ingredient can comprise at least 10% by dry weight of each of the at least two oligosaccharides, and at least 50% by dry weight of each of the at least two oligosaccharides.
- a foodstuff ingredient, cosmetic ingredient, or nutraceutical ingredient composition comprising at least two oligosaccharides selected from the list consisting of:
- cello-oligosaccharides having a degree of polymerisation of from two to six;
- xylo-oligosaccharides having a degree of polymerisation of from two to twelve
- mixed-linkage glucan oligosaccharides having a degree of polymerisation of from two to five;
- manno-oligosaccharides having a degree of polymerisation of from two to twelve
- xyloglucan oligosaccharides having a degree of polymerisation of from four to twelve
- chito-oligosaccharides having a degree of polymerisation of from two to twelve, wherein the composition comprises at least 10%, by dry weight of each of the at least two oligosaccharides, and wherein the ingredient comprises at least 50% by dry weight of the two or more oligosaccharides present.
- an oligosaccharide mixture in the formation of a foodstuff, cosmetic, or nutraceutical, wherein the oligosaccharide mixture comprises two oligosaccharides selected from the list consisting of: i) cello-oligosaccharides having a degree of polymerisation from two to six;
- xylo-oligosaccharides having a degree of polymerisation of from two to twelve
- mixed-linkage glucan oligosaccharides having a degree of polymerisation of from two to five;
- manno-oligosaccharides having a degree of polymerisation of from two to twelve
- xyloglucan oligosaccharides having a degree of polymerisation of from four to twelve
- chito-oligosaccharides having a degree of polymerisation of from two to twelve, wherein the two oligosaccharides are present in a ratio of from 1 :9 to 9:1, preferably from 1 :4 to 4:1, more preferably from 1 :3 to 3:1, most preferably 2:3 to 3:2, in relation to each other, optionally wherein the oligosaccharide mixture comprises third oligosaccharides selected from (i) to (vi), and wherein the ingredient comprises at least 50% by dry weight of the two or more oligosaccharides present.
- a method for producing a foodstuff ingredient, cosmetic ingredient, or nutraceutical ingredient, the ingredient comprising one or more oligosaccharides and one or more polysaccharides comprising the steps of:
- a) forming the one or more oligosaccharides and one or more polysaccharides by an enzymatic reaction comprising the step of contacting, in a solution or suspension, one or more polysaccharide-cleaving enzymes and one or more feedstocks, wherein the one or more feedstocks comprise sugar cane, com stover, com cob, wheat bran, wheat straw, hardwood, softwood, cellulose, chitin, chitosan, xylan, xyloglucan, mixed-linkage glucan, mannan, and/or lignocellulose;
- the method for producing an ingredient may include a washing step to separate oligosaccharide fractions before recombining the one or more oligosaccharides.
- a portion of the one or more oligosaccharides may be recombined with a portion of the one or more polysaccharides to form an ingredient.
- Preparing the foodstuff, cosmetic, or nutraceutical ingredient in this way can allow for efficient use of biomass by incorporating oligomeric and polymeric material from the same biomass source. Such preparation can also allow for optional purification, derivatisation and/or other modification, and/or control of oligomeric and polymeric proportions, which can improve the functional properties, nutritional properties, and/or tolerance of the ingredient.
- Figure 1 shows HPLC trace data of oligosaccharide compositions that are expected to be created after digestion with enzymes.
- Figure 2 shows cookies fresh out of the oven (panel a) and cut in half after a cooling period (panel b).
- the cookies were made using various compositions comprising combinations of cellobiose, xylo-oligosaccharides, and cellulose.
- Figure 3 shows the relative sweetness of various combinations of xylo-oligosaccharide- cellobiose in solution.
- Figure 4 shows solutions/suspensions of cellobiose at concentrations from 20-320 mg/mL after being vortexed for 30 seconds alone (panel a), or in the presence of half the concentration of xylo-oligosaccharides (panel b) or the same concentration of xylo-oligosaccharides (panel c).
- Figure 5 shows the hygroscopicity of various cellobiose-xylo-oligosaccharide compositions.
- Figure 6 shows the oligosaccharide profile analysed by thin-layer chromatography of the cello-oligosaccharide mixture produced by the enzymatic reaction on microcrystalline cellulose, and cakes made using the oligosaccharides with either the dried undigested microcrystalline cellulose from cellulolytic reactions or untreated microcrystalline cellulose.
- Figure 7 shows the oligosaccharide profile analysed by thin-layer chromatography of the oligosaccharide mixture produced by the enzymatic reaction on wheat bran lignocellulose, and cakes made using the undigested lignocellulose from cellulolytic reaction alone, the oligosaccharides from cellulolytic reaction alone, and the undigested lignocellulose from cellulolytic reaction in combination with oligosaccharides from cellulolytic reaction.
- Figure 8 shows the oligosaccharide profile analysed by thin-layer chromatography of the oligosaccharide mixture produced by the enzymatic reaction, and cakes made using the oligosaccharides from cellulolytic reaction along with the undigested lignocellulose from cellulolytic reactions or with fresh lignocellulose.
- Figure 9 shows colour images captured for samples 1, 2, 3, and 4 using a Digi Eye system.
- Figures 10A-10C show colour measurements of oligosaccharide samples.
- Figure 11 shows hygroscopicity profiles of samples 1, 2, 3, and 4.
- Figure 12 shows cohesion strength of samples 1, 2, 3, and 4.
- Figure 13 shows viscosity of cellobiose and xylo-oligosaccharide mixtures.
- Figure 14 shows examples of cream cheese icing made using oligosaccharide mixtures.
- Figure 15 shows examples of meringue made using oligosaccharide mixtures.
- Figure 16 shows examples of chocolate chip muffin or cupcakes made using oligosaccharide mixtures.
- Figure 17 shows examples of peanut butter cookie made using oligosaccharide mixtures.
- Figure 18 shows examples of jam made using oligosaccharide mixtures.
- saccharide compositions that can be useful in foodstuff, cosmetic, or nutraceutical products. Some embodiments of the present disclosure additionally offer such foodstuff, cosmetic, or nutraceutical products with novel properties.
- the saccharide compositions may be consumable compositions including cello-oligosaccharides, xylo-oligosaccharides, mixed-linkage glucan oligosaccharides, manno-oligosaccharides, and/or xyloglucan oligosaccharides.
- Such consumable compositions may be used as sweeteners (e.g., in a foodstuff), binders, and/or fibre content enhancers.
- “food” and“foodstuff’ refer to any item destined for consumption, which may be consumption by a human or by any other animal. It may be food, feed, a beverage, or an ingredient to be used in the production of any of the above.
- nutraceutical refers to any composition introduced into a human or other animal, whether by ingestion, injection, absorption, or any other method, for the purpose of providing nutrition to the human or other animal.
- Use of such a nutraceutical may take the form of a drink with added dietary fibre, a prebiotic additive, a pill or other capsule, or any other suitable use.
- cosmetic refers to any composition which is intended for use on humans or other animals to increase their aesthetic appeal or prevent future loss of aesthetic appeal, as well as any other compositions known in general parlance as cosmetics. Aesthetic appeal is not limited to visual aesthetics but applies as well to textural or any other appeal.
- the cosmetic may be mascara, foundation, lip gloss, eyeshadow, eyeliner, primer, lipstick blush, nail polish, bronzer, or any other makeup; shampoo, conditioner, styling mousse, styling gel, hairspray, hair dye, hair wax, or any other hair product; moisturiser, exfoliant, sun cream, cleanser, toothpaste, or a cream, a lotion, ointment or any other composition effective in modifying teeth, skin, hair, or other parts of the body in some aesthetic way.
- the cosmetic may be a composition used as a component of a face mask, brush, hair roller, other styling device, or other solid structure, or any other suitable composition.
- polysaccharide refers to a saccharide polymer of any length greater than about 20 residues.
- Polysaccharides may be highly branched, lightly branched, or unbranched, may comprise any manner of glycosidic bond in any combination, any number of, for example, a or b linkages, and any combination of monomer types, such as glucose, glucosamine, mannose, xylose, galactose, fucose, fructose, glucuronic acid, arabinose, or derivatives thereof such as any combination of the above monomers decorated with acetyl or other groups.
- the polysaccharide may be a cellulosic or hemicellulosic polymer, hemicellulosic polymers envisaged including xylan, glucuronoxylan, arabinoxylan, glucomannan, and xyloglucan.
- cellulose is the preferred cellulosic polymer.
- lignocellulose refers to polysaccharide-comprising aggregates that are, or are derived from, plant cell wall material.
- they may comprise one or more of the following polysaccharides associated together: cellulose, xylan, mannan, and mixed-linkage glucan.
- “highly branched,”“lightly branched,” and“unbranched” refer to the number of side-chains per stretch of main chain in a saccharide. Highly branched saccharides have on average from 4 to 10 side chains per 10 main-chain residues, slightly branched saccharides have on average from 1 to 3 side chains per 10 main-chain residues, and unbranched saccharides have only one main chain and no side chains. The average is calculated by dividing the number of side chains in a saccharide by the number of main-chain residues.
- saccharide refers to any polysaccharide and/or oligosaccharide, such as monosaccharide and/or disaccharide.
- oligosaccharide refers to saccharide polymers having chain lengths less than or equal to about 20 saccharide residues. Oligosaccharides may be highly branched, lightly branched, or unbranched, may comprise glycosidic bonds in any combination, any number of a or b linkages, and any combination of monomer types, such as glucose, glucosamine, mannose, xylose, galactose, fucose, fructose, glucuronic acid, arabinose, or derivatives thereof. Suitable derivatives include the above monomers comprising acetyl or other groups.
- “monosaccharide” and“disaccharide” refer to saccharide compounds consisting respectively of one or two residues.
- Monosaccharides are compounds such as glucose, glucosamine, xylose, galactose, fucose, fructose, glucuronic acid, arabinose, galacturonic acid; or epimers or other derivatives thereof. Suitable derivatives include acetyl or other groups.
- Disaccharides are compounds consisting of two monosaccharides joined via any glycosidic bond.
- “cello-oligosaccharides” refers to oligosaccharides composed of one or more glucose residues linked by b- 1 ,4-glycosidic bonds, and may be chemically related to that by oxidation, reduction, esterification, epimerisation, or another chemical modification.
- xylo-oligosaccharides refers to oligosaccharides composed primarily of xylose residues (typically linked by b-1,4 ⁇ 1goo8k1 ⁇ bonds) and may also contain glucuronic acid residues and/or arabinose residues and/or acetyl groups and/or any other modification, and may be chemically related to that by oxidation, reduction, esterification, epimerisation, or another chemical modification.
- mixed-linkage glucan-oligosaccharides refers to oligosaccharides composed of one or more glucose residues linked by at least one b-1,3 ⁇ 1goo8k1 ⁇ bond and at least one b-1,4 ⁇ 1ga 8k1k; bond, and may be chemically related to that by oxidation, reduction, esterification, epimerisation, or another chemical modification
- “manno-oligosaccharides” refers to oligosaccharides composed of one or more mannose residues and optionally containing one or more glucose and/or galactose residues, and may be chemically related to that by oxidation, reduction, esterification, epimerisation, or another chemical modification;
- chito-oligosaccharides refers to oligosaccharides composed of one or more glucosamine and/or N-acetyl-glucosamine residues, and may be chemically related to that by oxidation, reduction, esterification, epimerisation, or another chemical modification.
- “cellulose” refers to polysaccharides composed of glucose residues linked by b- 1 ,4-glycosidic bonds, and derivatives thereof.
- “Xylan” refers to polysaccharides composed of a backbone of xylose residues and may also contain glucuronic acid residues and/or arabinose residues and/or acetyl groups and/or any other modification.
- “Mixed-linkage glucan” refers to polysaccharides composed of glucose residues linked by b- 1 ,3-glycosidic bonds and b-1,4- glycosidic bonds.
- “Mannan” refers to polysaccharides composed of greater than 40% mannose residues and optionally containing glucose and/or galactose residues.
- “Chitin” or“chitosan” refer to polysaccharides composed of glucosamine and/or N-acetyl-glucosamine residues.
- the term“about” as used herein can mean within 1 or more than 1 standard deviation.
- “about” can mean a range of up to 10%, up to 5%, or up to 1% of a given value.
- about can mean up to ⁇ 10%, ⁇ 9%, ⁇ 8%, ⁇ 7%, ⁇ 6%, ⁇ 5%, ⁇ 4%, ⁇ 3%, ⁇ 2%, or ⁇ 1% of a given value.
- the polysaccharide components of the composition may comprise one or more of any type of polysaccharide.
- they comprise cellulose, xylan, mixed- linkage glucan, mannan, xyloglucan, chitin or chitosan, or derivatives of any of the aforementioned polysaccharides.
- the composition may comprise various oligosaccharides, and at varying amounts, depending on the desired properties.
- the composition may comprise at least 20% by dry weight, preferably at least 30% by dry weight, cello-oligosaccharides having a degree of polymerisation of from two to six and/or the composition may comprise at least 20% by dry weight, preferably at least 30% by dry weight, xylo-oligosaccharides having a degree of polymerisation of from two to twelve and/or the composition may comprise at least 20% by dry weight, preferably at least 30% by dry weight, mixed- linkage glucan oligosaccharides having a degree of polymerisation of from two to five, and/or the composition may comprise at least 20% by dry weight, preferably at least 30% by dry weight, manno-oligosaccharides having a degree of polymerisation of from two to twelve, and/or the composition may comprise at least 20% by dry weight, preferably at least 30% by dry weight, xyloglucan oligosaccharides, and at
- composition can comprise a maximum of 100% by dry weight of the above oligosaccharides, therefore the above embodiment, wherein the oligosaccharides are present in at least 20% by dry weight, does not comprise all six types of oligosaccharides.
- oligosaccharide mixture in the formation of a foodstuff, cosmetic, or nutraceutical, wherein the oligosaccharide mixture comprises two oligosaccharides selected from the list consisting of:
- cello-oligosaccharides having a degree of polymerisation of from two to six;
- xylo-oligosaccharides having a degree of polymerisation of from two to twelve
- mixed-linkage glucan oligosaccharides having a degree of polymerisation of from two to five;
- manno-oligosaccharides having a degree of polymerisation of from two to twelve
- xyloglucan oligosaccharides having a degree of polymerisation of from four to ten
- chito-oligosaccharides having a degree of polymerisation of from two to twelve, wherein the two oligosaccharides may be present in a ratio of from 1 :9 to 9:1, preferably 1 :4 to 4:1, more preferably from 2:3 to 3:2, in relation to each other.
- each of the oligosaccharides may be varied depending on the desired properties of the resulting foodstuff, cosmetic, or nutraceutical.
- the two oligosaccharides may be present in a ratio of 1 :9 to 9:1, preferably 1 :2 to 2:1, more preferably 2:3 to 3:2, in relation to each other.
- the oligosaccharide mixture may further comprise a third oligosaccharide and a fourth oligosaccharide.
- the oligosaccharide mixture may comprise a third oligosaccharide, a fourth oligosaccharide, and a fifth oligosaccharide.
- the oligosaccharide mixture may further comprise a third oligosaccharide, a fourth oligosaccharide, a fifth oligosaccharide, and a sixth oligosaccharide. These oligosaccharides may be selected from the same list as the at least two oligosaccharides as provided above.
- Preferred oligosaccharide mixtures of the at least two oligosaccharides may comprise the cello-oligosaccharides, for instance, cello-oligosaccharides in combination with the xylo- oligosaccharides.
- An alternative preferable composition may comprise cello-oligosaccharides in combination with manno-oligosaccharides.
- the oligosaccharide mixtures of the at least two oligosaccharides may additionally include a polysaccharide, preferably a cellulosic polysaccharide, such as cellulose, or a polysaccharide derivative, preferably a cellulose derivative, such as carboxymethylcellulose, or a polysaccharide aggregate, preferably a portion of lignocellulosic biomass.
- a polysaccharide preferably a cellulosic polysaccharide, such as cellulose, or a polysaccharide derivative, preferably a cellulose derivative, such as carboxymethylcellulose, or a polysaccharide aggregate, preferably a portion of lignocellulosic biomass.
- the ratio in the combination may be from 1 :100 to 1 :1 polysaccharide/polysaccharide derivative/polysaccharide aggregate:oligosaccharide, preferably from 1 :90 to 1 :2, preferably from 1 :80 to 1 :3, preferably from 1 :70 to 1 :4, and preferably from 1 :60 to 1 :5.
- the ratio between the first oligosaccharide, the second oligosaccharide, and the polysaccharide may be from 2:2:1 to 30:30:1, preferably about 3:3:1.
- a composition may comprise a mixture of one or more oligosaccharides.
- a mixture of oligosaccharides may comprise two forms of oligosaccharides, for instance, cello- oligosaccharides and xylo-oligosaccharides.
- a mixture of oligosaccharides may comprise three forms of oligosaccharides, for instance, cello-oligosaccharides, manno-oligosaccharides, and xylo-oligosaccharides.
- a mixture of oligosaccharides may comprise four forms of oligosaccharides, for instance, cello-oligosaccharides, manno-oligosaccharides, mixed-linkage glucan oligosaccharides, chito-oligosaccharides, and xylo-oligosaccharides.
- An oligosaccharide mixture may comprise two forms of oligosaccharides, for example, a first oligosaccharide and a second oligosaccharide.
- An oligosaccharide mixture may comprise about 5% of a first oligosaccharide and about 95% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 10% of a first oligosaccharide and about 90% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 15% of a first oligosaccharide and about 85% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 20% of a first oligosaccharide and about 80% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 25% of a first oligosaccharide and about 75% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 30% of a first oligosaccharide and about 70% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 35% of a first oligosaccharide and about 65% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 40% of a first oligosaccharide and about 50% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 45% of a first oligosaccharide and 55% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 50% of a first oligosaccharide and 50% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 55% of a first oligosaccharide and 45% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 60% of a first oligosaccharide and 30% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 65% of a first oligosaccharide and 35% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 70% of a first oligosaccharide and 30% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 75% of a first oligosaccharide and 25% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 80% of a first oligosaccharide and 20% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 85% of a first oligosaccharide and 15% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 90% of a first oligosaccharide and 10% of a second oligosaccharide w/w.
- An oligosaccharide mixture may comprise 95% of a first oligosaccharide and 5% of a second oligosaccharide w/w.
- a first oligosaccharide may be cello- oligosaccharides and a second oligosaccharide may be xylo-oligosaccharides.
- a first oligosaccharide may be cello-oligosaccharides and a second oligosaccharide may be manno-oligosaccharides.
- a first oligosaccharide may be xylo-oligosaccharides and a second oligosaccharide may be manno-oligosaccharides.
- Other combinations of a first oligosaccharide and a second oligosaccharide are also within the scope of this disclosure.
- An oligosaccharide mixture may comprise three forms of oligosaccharides, for example a first oligosaccharide, a second oligosaccharide, and a third oligosaccharide.
- An oligosaccharide mixture may comprise about 20% of a first oligosaccharide, 40% of a second oligosaccharide, and 40% of a third oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 30% of a first oligosaccharide, 30% of a second oligosaccharide, and 40% of a third oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 10% of a first oligosaccharide, 10% of a second oligosaccharide, and 80% of a third oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 20% of a first oligosaccharide, 20% of a second oligosaccharide, and 60% of a third oligosaccharide w/w.
- An oligosaccharide mixture may comprise about 20% of a first oligosaccharide, 30% of a second oligosaccharide, and 50% of a third oligosaccharide w/w.
- a first oligosaccharide may be manno-oligosaccharides
- a second oligosaccharide may be xylo-oligosaccharides
- a third oligosaccharide may be cello-oligosaccharides.
- a first oligosaccharide may be xyloglucan-oligosaccharides
- a second oligosaccharide may be xylo-oligosaccharides
- a third oligosaccharide may be cello- oligosaccharides.
- An oligosaccharide mixture may comprise two or more oligosaccharides, a first oligosaccharide and a second oligosaccharide which is different than the first oligosaccharide.
- the first oligosaccharide may be a xylo-oligosaccharide or a cello-oligosaccharide or a manno-oligosaccharide or other oligosaccharides as provided herein whereas the second oligosaccharide can be a xylo-oligosaccharide or a cello-oligosaccharide or a manno- oligosaccharide or other oligosaccharides not used as the first oligosaccharides.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 1:1.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 1:2.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 1:3.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 1:4.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 1:5.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 1:6.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 1:7.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 1:8.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 1 :9.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 2:1.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 2:3.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 2:5.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 2:7.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 2:9.
- the oligosaccharides may be cello-oligosaccharides, manno-oligosaccharides, xylo- oligosaccharides, xyloglucan-oligosaccharides, mixed-linkage oligosaccharides, chito- oligosaccharides or other oligosaccharides as provided herein wherein the first oligosaccharide is selected to be a different oligosaccharide than the second oligosaccharide.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 3:1.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 3:2.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 3:4.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 3:5.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 3:7.
- the ratio of a first oligosaccharide to a second oligosaccharide in the mixture may be about 3:8.
- the oligosaccharides may be cello-oligosaccharides, manno-oligosaccharides, xylo- oligosaccharides, xyloglucan-oligosaccharides, mixed-linkage oligosaccharides, chito- oligosaccharides or other oligosaccharides provided herein wherein the first oligosaccharide is selected to be a different oligosaccharide than the second oligosaccharide.
- the ratio of a first oligosaccharide to a second oligosaccharide in an oligosaccharide mixture comprising two or more oligosaccharides may be from 1 :9 to 9:1.
- the ratio of a first oligosaccharide to a second oligosaccharide may be from 1 :4 to 4:1.
- the ratio of a first oligosaccharide to a second oligosaccharide may be from 1 :3 to 3:1.
- the ratio of a first oligosaccharide to a second oligosaccharide may be from 2:3 to 3:2.
- the oligosaccharides may be cello-oligosaccharides, manno-oligosaccharides, xylo-oligosaccharides, xyloglucan- oligosaccharides, mixed-linkage oligosaccharides, chito-oligosaccharides or other oligosaccharides provided herein wherein the first oligosaccharide is selected to be a different oligosaccharide than the second oligosaccharide.
- the concentration of xylo-oligosaccharides with a degree of polymerization of two in a xylo-oligosaccharide mixture may be about 2% to about 80% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of two may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 18%, 20%, 25%, or 30% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of two may be higher in some cases, for instance, up to 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, or 80% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of three in a xylo-oligosaccharide mixture may be about 2% to about 20% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of three may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of four in a xylo-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of four may be at least 5%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of five in a xylo-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of five may be at least 5%, 7%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of six in a xylo-oligosaccharide mixture may be about 5% to about 25% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of six may be at least 5%, 8%, 10%, 12%, 15%, 18%, 20%, or 25% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of seven in a xylo-oligosaccharide mixture may be about 2% to about 20% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of seven may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 17%, or 20% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of eight in a xylo-oligosaccharide mixture may be about 1% to about 15% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of eight may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of nine in a xylo-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of nine may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of ten in a xylo-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of ten may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of eleven in a xylo-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of eleven may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of xylo-oligosaccharides with a degree of polymerization of twelve in a xylo-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of xylo- oligosaccharides with a degree of polymerization of twelve may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of cello-oligosaccharides with a degree of polymerization of two in a cello-oligosaccharide mixture may be about 2% to about 80% w/w.
- the concentration of cello- oligosaccharides with a degree of polymerization of two may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 18%, 20%, 25%, or 30% w/w.
- the concentration of cello-oligosaccharides with a degree of polymerization of two may be higher in some cases, for instance, at least 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, or 80% w/w.
- the concentration of cello-oligosaccharides with a degree of polymerization of three in a cello-oligosaccharide mixture may be about 2% to about 20% w/w.
- the concentration of cello- oligosaccharides with a degree of polymerization of three may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of cello-oligosaccharides with a degree of polymerization of four in a cello-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of cello- oligosaccharides with a degree of polymerization of four may be at least 5%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of cello-oligosaccharides with a degree of polymerization of five in a cello-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of cello- oligosaccharides with a degree of polymerization of five may be at least 5%, 7%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of cello-oligosaccharides with a degree of polymerization of six in a cello-oligosaccharide mixture may be about 5% to about 25% w/w.
- the concentration of cello- oligosaccharides with a degree of polymerization of six may be at least 5%, 8%, 10%, 12%, 15%, 18%, 20%, or 25% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of two in a manno-oligosaccharide mixture may be about 2% to about 30% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of two may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 18%, 20%, 25%, or 30% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of three in a manno-oligosaccharide mixture may be about 2% to about 20% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of three may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of four in a manno-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of four may be at least 5%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of five in a manno-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of five may be at least 5%, 7%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of six in a manno-oligosaccharide mixture may be about 5% to about 25% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of six may be at least 5%, 8%, 10%, 12%, 15%, 18%, 20%, or 25% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of seven in a manno-oligosaccharide mixture may be about 2% to about 20% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of seven may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 17%, or 20% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of eight in a manno-oligosaccharide mixture may be about 1% to about 15% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of eight may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of nine in a manno-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of nine may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of ten in a manno-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of ten may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of eleven in a manno-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of eleven may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of twelve in a manno-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of manno-oligosaccharides with a degree of polymerization of twelve may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of four in a xyloglucan-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of four may be at least 5%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of five in a xyloglucan-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of five may be at least 5%, 7%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of six in a xyloglucan-oligosaccharide mixture may be about 5% to about 25% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of six may be at least 5%, 8%, 10%, 12%, 15%, 18%, 20%, or 25% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of seven in a xyloglucan-oligosaccharide mixture may be about 2% to about 20% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of seven may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 17%, or 20% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of eight in a xyloglucan-oligosaccharide mixture may be about 1% to about 15% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of eight may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of nine in a xyloglucan-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of nine may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of ten in a xyloglucan-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of xyloglucan-oligosaccharides with a degree of polymerization of ten may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of mixed-linkage glucan-oligosaccharides with a degree of polymerization of two in a mixed-linkage glucan-oligosaccharide mixture may be about 2% to about 30% w/w.
- the concentration of mixed-linkage glucan-oligosaccharides with a degree of polymerization of two may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 18%, 20%, 25%, or 30% w/w.
- the concentration of mixed-linkage glucan-oligosaccharides with a degree of polymerization of three in a mixed-linkage glucan-oligosaccharide mixture may be about 2% to about 20% w/w.
- the concentration of mixed-linkage glucan-oligosaccharides with a degree of polymerization of three may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of mixed-linkage glucan-oligosaccharides with a degree of polymerization of four in a mixed- linkage glucan-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of mixed-linkage glucan-oligosaccharides with a degree of polymerization of four may be at least 5%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of mixed-linkage glucan-oligosaccharides with a degree of polymerization of five in a mixed- linkage glucan-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of mixed-linkage glucan-oligosaccharides with a degree of polymerization of five may be at least 5%, 7%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of two in a chito-oligosaccharide mixture may be about 2% to about 30% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of two may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 18%, 20%, 25%, or 30% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of three in a chito-oligosaccharide mixture may be about 2% to about 20% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of three may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of four in a chito-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of four may be at least 5%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of five in a chito-oligosaccharide mixture may be about 5% to about 20% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of five may be at least 5%, 7%, 8%, 10%, 12%, 15%, 18%, or 20% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of six in a chito-oligosaccharide mixture may be about 5% to about 25% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of six may be at least 5%, 8%, 10%, 12%, 15%, 18%, 20%, or 25% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of seven in a chito-oligosaccharide mixture may be about 2% to about 20% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of seven may be at least 2%, 4%, 6%, 8%, 10%, 12%, 15%, 17%, or 20% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of eight in a chito-oligosaccharide mixture may be about 1% to about 15% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of eight may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of nine in a chito-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of nine may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of ten in a chito-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of ten may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10% or 15% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of eleven in a chito-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of eleven may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- the concentration of chito-oligosaccharides with a degree of polymerization of twelve in a chito-oligosaccharide mixture may be about 2% to about 15% w/w.
- the concentration of chito- oligosaccharides with a degree of polymerization of twelve may be at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or 15% w/w.
- compositions with combinations of polysaccharides and oligosaccharides are provided.
- a composition may comprise a combination of polysaccharides and oligosaccharides.
- the source of the polysaccharides in such compositions may contain cellulose, such as plant biomass, for example the undigested component of partially digested plant biomass, such as the undigested plant biomass from the same reaction as that which produced the oligosaccharides.
- the polysaccharides in the undigested biomass may comprise lignin, polyphenol, cellulose, lignocellulose, or any other suitable polysaccharides as described herein. Addition of polysaccharides to oligosaccharide mixtures can be done to improve the gastrointestinal tolerance of the oligosaccharide mixtures.
- Oligosaccharide consumption can cause gastrointestinal distress, including diarrhea, discomfort, and bloating.
- the compositions described herein may have an improved gastrointestinal tolerance such as, less or no discomfort, bloating, diarrhea or gastrointestinal distress as compared to a saccharide composition available commercially or a saccharide composition comprising primarily monosaccharides and/or disaccharides.
- the concentration of undigested biomass in a composition may be 1% to 50% w/w.
- the concentration of undigested biomass in a composition may be 1% to 5%, 1% to 10%, 1% to 15%, 1% to 20%, 1% to 25%, 1% to 30%, 1% to 35%, 1% to 40%, 1% to 45%, 1% to 50%, 5% to 10%, 5% to 15%, 5% to 20%, 5% to 25%, 5% to 30%, 5% to 35%, 5% to 40%, 5% to 45%, 5% to 50%, 10% to 15%, 10% to 20%, 10% to 25%, 10% to 30%, 10% to 35%, 10% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 15% to 30%, 15% to 35%, 15% to 40%, 15% to
- the concentration of undigested biomass in a composition may be 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of undigested biomass in a composition may be at least 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or 45% w/w.
- the concentration of undigested biomass in a composition may be at most 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of xylo-oligosaccharides in a composition may be 1% to 50% w/w.
- the concentration of xylo-oligosaccharides in a composition may be 1% to 5%, 1% to 10%, 1% to 15%, 1% to 20%, 1% to 25%, 1% to 30%, 1% to 35%, 1% to 40%, 1% to 45%, 1% to 50%, 5% to 10%, 5% to 15%, 5% to 20%, 5% to 25%, 5% to 30%, 5% to 35%, 5% to 40%, 5% to 45%, 5% to 50%, 10% to 15%, 10% to 20%, 10% to 25%, 10% to 30%, 10% to 35%, 10% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 15% to 30%, 15% to 35%, 15% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 15% to 30%, 15% to 35%, 15% to
- the concentration of xylo-oligosaccharides in a composition may be 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of xylo-oligosaccharides in a composition may be at least 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or 45% w/w.
- the concentration of xylo-oligosaccharides in a composition may be at most 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of cello-oligosaccharides in a composition may be 1% to 50% w/w.
- the concentration of cello-oligosaccharides in a composition may be 1% to 5%, 1% to 10%, 1% to 15%, 1% to 20%, 1% to 25%, 1% to 30%, 1% to 35%, 1% to 40%, 1% to 45%, 1% to 50%, 5% to 10%, 5% to 15%, 5% to 20%, 5% to 25%, 5% to 30%, 5% to 35%, 5% to 40%, 5% to 45%, 5% to 50%, 10% to 15%, 10% to 20%, 10% to 25%, 10% to 30%, 10% to 35%, 10% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 15% to 30%, 15% to 35%, 15% to
- the concentration of cello-oligosaccharides in a composition may be 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of cello-oligosaccharides in a composition may be at least 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or 45% w/w.
- the concentration of cello-oligosaccharides in a composition may be at most 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of manno-oligosaccharides in a composition may be 1% to 50% w/w.
- the concentration of manno-oligosaccharides in a composition may be 1% to 5%, 1% to 10%, 1% to 15%, 1% to 20%, 1% to 25%, 1% to 30%, 1% to 35%, 1% to 40%, 1% to 45%, 1% to 50%, 5% to 10%, 5% to 15%, 5% to 20%, 5% to 25%, 5% to 30%, 5% to 35%, 5% to 40%, 5% to 45%, 5% to 50%, 10% to 15%, 10% to 20%, 10% to 25%, 10% to 30%, 10% to 35%, 10% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 15% to 30%, 15% to 35%, 15% to
- the concentration of manno-oligosaccharides in a composition may be 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of manno-oligosaccharides in a composition may be at least 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or 45% w/w.
- the concentration of manno-oligosaccharides in a composition may be at most 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of chito-oligosaccharides in a composition may be 1% to 50% w/w.
- the concentration of chito-oligosaccharides in a composition may be 1% to 5%, 1% to 10%, 1% to 15%, 1% to 20%, 1% to 25%, 1% to 30%, 1% to 35%, 1% to 40%, 1% to 45%, 1% to 50%, 5% to 10%, 5% to 15%, 5% to 20%, 5% to 25%, 5% to 30%, 5% to 35%, 5% to 40%, 5% to 45%, 5% to 50%, 10% to 15%, 10% to 20%, 10% to 25%, 10% to 30%, 10% to 35%, 10% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 15% to 30%, 15% to 35%, 15% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 15% to 30%, 15% to 35%, 15% to
- the concentration of chito-oligosaccharides in a composition may be 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of chito-oligosaccharides in a composition may be at least 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or 45% w/w.
- the concentration of chito-oligosaccharides in a composition may be at most 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of xyloglucan-oligosaccharides in a composition may be 1% to 50% w/w.
- the concentration of xyloglucan-oligosaccharides in a composition may be 1% to 5%, 1% to 10%, 1% to 15%, 1% to 20%, 1% to 25%, 1% to 30%, 1% to 35%, 1% to 40%, 1% to 45%, 1% to 50%, 5% to 10%, 5% to 15%, 5% to 20%, 5% to 25%, 5% to 30%, 5% to 35%, 5% to 40%, 5% to 45%, 5% to 50%, 10% to 15%, 10% to 20%, 10% to 25%, 10% to 30%, 10% to 35%, 10% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 15% to 30%, 15% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 15% to 30%, 15% to 15% to 30%, 15% to
- the concentration of xyloglucan- oligosaccharides in a composition may be 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of xyloglucan-oligosaccharides in a composition may be at least 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or 45% w/w.
- the concentration of xyloglucan- oligosaccharides in a composition may be at most 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of mixed- linkage glucan-oligosaccharides in a composition may be 1% to 50% w/w.
- the concentration of mixed- linkage glucan-oligosaccharides in a composition may be 1% to 5%, 1% to 10%, 1% to 15%, 1% to 20%, 1% to 25%, 1% to 30%, 1% to 35%, 1% to 40%, 1% to 45%, 1% to 50%, 5% to 10%, 5% to 15%, 5% to 20%, 5% to 25%, 5% to 30%, 5% to 35%, 5% to 40%, 5% to 45%, 5% to 50%, 10% to 15%, 10% to 20%, 10% to 25%, 10% to 30%, 10% to 35%, 10% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 10% to 30%, 10% to 35%, 10% to 40%, 10% to 45%, 10% to 50%, 15% to 20%, 15% to 25%, 15% to 30%, 10% to 35%, 10% to 40%, 10% to 45%, 10% to 50%, 15% to 20%
- the concentration of mixed- linkage glucan-oligosaccharides in a composition may be 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- the concentration of mixed-linkage glucan-oligosaccharides in a composition may be at least 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or 45% w/w.
- the concentration of mixed-linkage glucan-oligosaccharides in a composition may be at most 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w.
- a composition may comprise polysaccharides and one or more oligosaccharides.
- the composition may comprise a polysaccharide and one type of oligosaccharide.
- the composition may comprise a polysaccharide and two forms of oligosaccharides.
- the composition may comprise a polysaccharide and three forms of oligosaccharides.
- the composition may comprise a polysaccharide and four forms of oligosaccharides.
- the composition may comprise a polysaccharide and five forms of oligosaccharides.
- the oligosaccharides may be xylo- oligosaccharides, cello-oligosaccharides, manno-oligosaccharides, xyloglucan-oligosaccharides, chito-oligosaccharides, or any other suitable oligosaccharides described herein.
- the composition may comprise about 5% to 50% polysaccharides w/w, such as in the type of undigested biomass, and about 5% to about 95% oligosaccharides w/w.
- the composition of polysaccharides may be at least about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% w/w w/w.
- Oligosaccharides in such mixtures may be present at greater than 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, or 95% w/w.
- the oligosaccharides may be a mixture of one or more oligosaccharides.
- a composition may comprise 5% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- the composition may comprise about 5% polysaccharides w/w, such as in the type of undigested biomass, and about 5% to about 95% oligosaccharides w/w. Oligosaccharides in such mixtures may be present at greater than 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or 95% w/w.
- the oligosaccharides may be a mixture of one or more oligosaccharides. For instance, a composition may comprise 5% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- the composition may comprise about 7% polysaccharides w/w, such as in the type of undigested biomass and about 5% to about 93% oligosaccharides w/w. Oligosaccharides may form at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or 93% w/w of such mixtures.
- the oligosaccharides may be a mixture of one or more oligosaccharides.
- a composition may comprise 7% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- the composition may comprise about 10% polysaccharides w/w, such as in the type of undigested biomass and about 5% to about 90% oligosaccharides w/w. Oligosaccharides may form at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85% or 90% w/w of such mixtures.
- the oligosaccharides may be a mixture of one or more oligosaccharides.
- a composition may comprise 10% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- the composition may comprise about 12% polysaccharides w/w, such as in the type of undigested biomass and about 5% to about 95% oligosaccharides w/w. Oligosaccharides may form at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85% or 88% w/w of such mixtures.
- the oligosaccharides may be a mixture of one or more oligosaccharides.
- a composition may comprise 12% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- the composition may comprise about 15% polysaccharides w/w, such as in the type of undigested biomass and about 5% to about 85% oligosaccharides w/w. Oligosaccharides may form at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80% or 85% w/w of such mixtures.
- the oligosaccharides may be a mixture of one or more oligosaccharides.
- a composition may comprise 15% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- the composition may comprise about 20% polysaccharides w/w, such as in the type of undigested biomass and about 5% to about 80% oligosaccharides w/w. Oligosaccharides may form at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75% or 80% w/w of such mixtures.
- the oligosaccharides may be a mixture of one or more oligosaccharides.
- a composition may comprise 20% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- the composition may comprise about 25% polysaccharides w/w, such as in the type of undigested biomass and about 5% to about 75% oligosaccharides w/w. Oligosaccharides may form at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70% or 75% w/w of such mixtures.
- the oligosaccharides may be a mixture of one or more oligosaccharides.
- a composition may comprise 25% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- the composition may comprise about 30% polysaccharides w/w, such as in the type of undigested biomass and about 5% to about 70% oligosaccharides w/w. Oligosaccharides may form at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65% or 70% w/w of such mixtures.
- the oligosaccharides may be a mixture of one or more oligosaccharides.
- a composition may comprise 30% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- the composition may comprise about 40% polysaccharides w/w, such as in the type of undigested biomass and about 5% to about 60% oligosaccharides w/w. Oligosaccharides may form at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55% or 60% w/w of such mixtures.
- the oligosaccharides may be a mixture of one or more oligosaccharides.
- a composition may comprise 40% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- the composition may comprise about 50% polysaccharides w/w, such as in the type of undigested biomass and about 5% to about 50% oligosaccharides w/w. Oligosaccharides may form at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or 50% w/w of such mixtures.
- the oligosaccharides may be a mixture of one or more oligosaccharides.
- a composition may comprise 50% undigested biomass and 50% oligosaccharide mixture w/w as described elsewhere herein.
- compositions are an ingredient.
- “ingredient” is any composition suitable for incorporation into a foodstuff, cosmetic, or nutraceutical product, which may include those which are used directly as the product itself
- the ingredient comprises at least 50%, 60%, 70%, 80%, 90%, 95%, 99%, 99.5% by dry weight of saccharide present.
- the ingredient may consist essentially of saccharides.
- “consist essentially of’ means that the material (for instance the ingredient) has less than 0.5% by dry weight, such as 0.3% by dry weight, for instance 0.1% by dry weight, of other substances.
- the ingredient may comprise an oligosaccharide mixture as described elsewhere herein.
- the ingredient may comprise at least two of the oligosaccharides. For instance, it may comprise three of the oligosaccharides. It may comprise four oligosaccharides. It may comprise five oligosaccharides. It may comprise six oligosaccharides.
- the ingredient comprises cello-oligosaccharides, for instance cello- oligosaccharides in combination with the xylo-oligosaccharides.
- An alternative ingredient may comprise cello-oligosaccharides in combination with manno-oligosaccharides.
- Ingredients may be used to prepare finished products.
- the ingredient may also be treated in some physical or chemical way before or during incorporation into a foodstuff, cosmetic, or nutraceutical. It may be directly incorporated into a product, or it may be incorporated into, for example, a dough, cake mixture, chocolate mixture, or other foodstuff precursor; a cosmetic base composition; or a nutraceutical, and be optionally cooked or otherwise treated in a way which may cause chemical modification, a change of texture a change of colour, or other modification.
- a foodstuff, cosmetic, or nutraceutical may be produced from an ingredient described herein.
- the saccharide formulations produced by the current method may be used as sweeteners, bulking agents, added dietary fibre, or humectants.
- the ingredient may be used as a sugar substitute.
- the ingredient may be incorporated into cakes, bread, or other baked goods, or into chocolate or other confectionery such as toffee, fudge, meringue, jam, jelly or caramel; or drinks, for example, to provide favourable taste or colour characteristics or to increase dietary fibre content.
- they may be incorporated into animal feed, for example either as an isolated ingredient or by utilising the enzymatic reaction mixture directly as feed.
- saccharides can be useful as ingredients, as they may improve texture and moisture retention, act as UV-absorbing molecules, maintain a gel or cream structure, and/or serve as bulking agents.
- the compositions described herein can be incorporated into nutraceutical compositions, as the dietary fibre they provide has been shown to encourage digestive health, well-regulated gut flora, and other benefits to wellbeing. In this context, they may also function as an ingredient in a probiotic drink or other prebiotic or probiotic formulation.
- compositions or ingredients as described herein may be used to alter one or more properties of the finished product.
- properties include, but are not limited to, sweetness, texture, mouthfeel, binding, glazing, smoothness, moistness, viscosity, color, hygroscopicity, flavor, bulking, water-retention, caramelization, surface texture, crystallization, structural properties and dissolution.
- compositions and/or ingredients described herein may provide a property to a finished product which is comparable to or better than the same property as provided by a saccharide mixture comprising primarily monosaccharides and/or disaccharides.
- the control composition may be a saccharide used commonly in consumables, for instance, a monosaccharide composition such as glucose, fructose, etc, a disaccharide composition such as sucrose or an artificial sugar composition.
- the term“comparable” as used herein may mean that the two compositions may be up to 100%, up to 95%, up to 90%, up to 80% identical. For instance, comparable can mean that the composition is up to 90% identical to the control composition.
- compositions described herein may be used as sweetener compositions.
- Sweetener compositions may be used by themselves or as an ingredient in a finished product.
- the compositions described herein may provide about the same level of sweetness or greater sweetness than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the compositions described herein may be used to replace the control composition as the sweetener in a finished product.
- the sweetness of a composition may be 5%, 10%, 15%, 20%, 30%, 40%, 50%, 70%, 80%, 90% or 100% more than an identical amount of the control composition.
- compositions described herein may provide a comparable flavor profile or better flavor profile than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the compositions described herein may be used to replace the control composition as a flavor enhancer in a finished product.
- the flavor of a composition may be 5%, 10%, 15%, 20%, 30%, 40%, 50%, 70%, 80%, 90% or 100% more than an identical amount of the control composition.
- compositions described herein may provide a comparable texture profile or better texture profile than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the compositions described herein may be used to replace the control composition as a texture enhancer in a finished product.
- the compositions described herein may provide a comparable binding profile or better binding profile than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the compositions described herein may be used to replace the control composition as a binding enhancer in a finished product.
- compositions described herein may provide a comparable glazing profile or better glazing profile than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the compositions described herein may be used to replace the control composition as a glazing enhancer in a finished product.
- compositions described herein may provide a comparable moistness or better moistness than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the compositions described herein may be used to replace the control composition to provide moistness in a finished product.
- compositions described herein may provide a comparable color profile or better color profile than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the compositions described herein may be used to replace the control composition as a color enhancer in a finished product.
- compositions described herein may provide a comparable dissolution profile or better dissolution profile than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the compositions described herein may be used to replace the control composition as a dissolution enhancer in a finished product.
- the dissolution of a composition may be 5%, 10%, 15%, 20%, 30%, 40%, 50%, 70%, 80%, 90% or 100% more than an identical amount of the control composition.
- compositions described herein may provide a comparable mouthfeel or better mouthfeel than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- compositions described herein may provide a comparable viscosity or better viscosity than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- compositions described herein may provide a comparable hygroscopicity or better hygroscopicity than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the hygroscopicity of a composition may be 5%, 10%, 15%, 20%, 30%, 40%, 50%, 70%, 80%, 90% or 100% more than an identical amount of the control composition.
- compositions described herein may provide a comparable water-retention or better water-retention than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the water -retention of a composition may be 5%, 10%, 15%, 20%, 30%, 40%, 50%, 70%, 80%, 90% or 100% more than an identical amount of the control composition.
- compositions described herein may provide a lower calorie composition than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the calorie count of a composition may be 5%, 10%, 15%, 20%, 30%, 40%, 50%, 70%, 80%, 90% or 100% less than an identical amount of the control composition.
- compositions described herein may provide a lower glycemic index than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the glycemic index of a composition may be 5%, 10%, 15%, 20%, 30%, 40%, 50%, 70%, 80%, 90% or 100% less than an identical amount of the control composition.
- compositions described herein may provide a comparable bulking or better bulking than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- compositions described herein may provide a comparable caramelization or better caramelization than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- compositions described herein may provide a comparable surface texture or better surface texture than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- compositions described herein may provide a comparable crystallization or better crystallization than an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- compositions described herein may provide comparable structural properties as an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- compositions described herein may provide less aftertaste compared to an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- compositions of oligosaccharides may have improved dissolution profiles, hygroscopicity profiles, and taste profiles compared to the oligosaccharides used alone.
- compositions or ingredients as described herein may be used to increase the fibre content of a finished product such as a foodstuff or a nutraceutical.
- the compositions may provide a higher level of fibre in the finished product as compared to an identical amount of a control composition wherein the control composition comprises primarily monosaccharides and/or disaccharides.
- the compositions may improve the fibre content of the finished product without negatively affecting any other properties such as taste, sweetness, mouthfeel, texture, binding, or any other properties described herein.
- the fibre content of a composition may be 5%, 10%, 15%, 20%, 30%, 40%, 50%, 70%, 80%, 90% or 100% more than an identical amount of the control composition.
- ingredients may be used to alter the properties of a finished product such as foodstuff or nutraceutical or cosmetic.
- the finished products may additionally comprise a polysaccharide, preferably a cellulosic polysaccharide, such as cellulose, or a polysaccharide derivative, preferably a cellulose derivative, such as carboxymethylcellulose, or a polysaccharide aggregate, preferably a portion of lignocellulosic biomass.
- the finished products can comprise from greater than 0% to 40% by dry weight of polysaccharide, polysaccharide derivative, or polysaccharide aggregate, preferably from greater than 1% to 30% by dry weight of polysaccharide, polysaccharide derivative, or polysaccharide aggregate, preferably from greater than 5% to 25% by dry weight of polysaccharide, polysaccharide derivative, or polysaccharide aggregate, preferably from greater than 10% to 20% by dry weight of polysaccharide, polysaccharide derivative, or polysaccharide aggregate.
- the concentration of a composition comprising polysaccharides and a mixture of oligosaccharides in a finished product may be anywhere from 0.1% to 40% w/w.
- the concentration of a composition comprising polysaccharides and a mixture of oligosaccharides in a finished product may be about 0.1% to about 0.5%, about 0.1% to about 1%, about 0.1% to about 5%, about 0.1% to about 10%, about 0.1% to about 15%, about 0.1% to about 20%, about 0.1% to about 25%, about 0.1% to about 30%, about 0.1% to about 35%, about 0.1% to about 40%, about 0.5% to about 1%, about 0.5% to about 5%, about 0.5% to about 10%, about 0.5% to about 15%, about 0.5% to about 20%, about 0.5% to about 25%, about 0.5% to about 30%, about 0.5% to about 35%, about 0.5% to about 40%, about 1% to about 5%, about 1% to about 10%, about 1% to about 15%, about 1% to about 20%, about 1% to about 25%, about
- the concentration of a composition comprising polysaccharides and a mixture of oligosaccharides in a finished product may be about 0.1%, about 0.5%, about 1%, about 5%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, or about 40% w/w.
- the concentration of a composition comprising polysaccharides and a mixture of oligosaccharides in a finished product may be at least 0.1%, 0.5%, 1%, 5%, 10%, 15%, 20%, 25%, 30%, or 35% w/w.
- the concentration of a composition comprising polysaccharides and a mixture of oligosaccharides in a finished product may be at most 0.5%, 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, or 40% w/w.
- One step of the method of forming or manufacturing the composition??? may be an enzymatic reaction, in which one or more enzymes are placed in a suitable reaction vessel together with one or more feedstocks, which may be soluble or insoluble in water, and a suitable solvent.
- the enzymatic reaction comprises a cellulase, an endo-glucanase, a cellobiohydrolase, a lytic polysaccharide monooxygenase (LPMO), a lichenase, a xyloglucan endoglucanase (XEG), a mannanase, a chitinase, and/or a xylanase.
- LPMO lytic polysaccharide monooxygenase
- XEG xyloglucan endoglucanase
- mannanase a chitinase
- a xylanase a variety of enzymes may be suitable for use in the enzymatic reaction.
- the enzymatic reaction comprises a cellulolytic preparation from a species, such as Trichoderma reesei, which may be purified and/or pre-treated and/or may be supplemented with one or more additional enzymes, for example, adding a beta-glucanase (SEQ ID NO: 14), a beta-xylanase (SEQ ID NO: 16) and a cellobiohydrolase, or a beta-glucanase, a beta-xylanase, an LPMO and a cellobiohydrolase, or an LPMO and a xylanase, or an LPMO, a xylanase, and a lichenase.
- a beta-glucanase SEQ ID NO: 14
- a beta-xylanase SEQ ID NO: 16
- cellobiohydrolase or a beta-glucanase, a beta-xylanase, an LPMO and
- Each enzyme may be provided to the enzymatic reaction as a purified enzyme, a semi-purified mixture derived from some natural source or lab-grown culture, in the form of a microbial strain engineered to produce the enzyme, or in any other manner. Fusions of these enzymes, either with other enzymes or with non-enzymatic modules such as carbohydrate- binding modules (CBMs), are also envisaged within each respective term, for example, an LPMO fused to a CBM, a xylanase fused to a CBM, or a xylanase fused to an LPMO.
- CBMs carbohydrate- binding modules
- “cellulase” refers to an enzyme that has, or a group of enzymes that collectively have, hydrolytic activity against cellulose, for example, an enzyme preparation containing endo-l,4-beta-glucanase, cellobiohydrolase, and/or beta-glucosidase activities.
- Such enzymes may be able to cleave glycosidic bonds in one or more forms of cellulose, including cellulose found in plant biomass. In doing so, they can produce products including glucose and cello-oligosaccharides.
- cellobiohydrolase refers to an enzyme that has hydrolytic activity against cellulose and produces mainly cellobiose as a product.
- Cellobiose is a disaccharide and is a cello-oligosaccharide.
- Such enzymes are able to cleave glycosidic bonds in one or more forms of cellulose, including cellulose found in plant biomass.
- Preferable cellobiohydrolases are from the GH6 and GH7 enzyme families, such as cellobiohydrolase 12 and 13 from Aspergillus niger (SEQ ID NO:20 and 21) more preferably, Cel6A or Cel7A enzymes derived from Trichoderma reesei (SEQ ID NOs:lO and 11).
- beta-glucosidase refers to an enzyme that has hydrolytic activity against cellulose and produces mainly glucose as a product. Such enzymes are able to cleave glycosidic bonds in one or more forms of cellulose, including cellulose found in plant biomass.
- Preferred beta-glucosidases include GH3 beta-glucosidases from Trichoderma reesei (SEQ ID NO:22).
- “lytic polysaccharide monooxygenase” and“LPMO” refer to a class of enzymes able to oxidatively cleave polysaccharides using a copper comprising moiety and using an oxygen source, such as a molecule of dioxygen, peroxide, or any other oxygen source; and a suitable reducing agent.
- an oxygen source such as a molecule of dioxygen, peroxide, or any other oxygen source
- a suitable reducing agent such as a molecule of dioxygen, peroxide, or any other oxygen source.
- Suitable reducing agents are not particularly limited, but examples include ascorbic acid, gallic acid, cysteine, NADH, NADPH, pyrogallol, dithiothreitol, cyanoborohydrides, borohydrides, photosynthetic pigments, lignin, lignols, and a combination of cellobiose and cellobiose dehydrogenase. While the skilled person knows a wide variety of photosynthetic pigments which may be used, thylakoids and purified fractions, or chlorophyllin, are preferred, and light may be supplied.
- LPMOs are selected from the following families: AA9, AA10, AA11, AA13, AA14, and AA15.
- the LPMO is PaLPM09E (SEQ ID NO:l), an AA9 LPMO originally isolated from the ascomycete fimgus Podospora anserina. More preferably still, the LPMO is an AA9 LPMO from Trichoderma reesei (SEQ ID NO:25).
- Aerobic conditions may comprise the addition of oxygen, which may be provided by aeration of the substrate mixture with an oxygen-comprising gas, such as air.
- Aeration may be conducted by the introduction of oxygen-comprising air bubbles into the aqueous substrate mixtures by various systems, such as an air-injector, an aeration frit, a membrane system, or an internal-loop airlift reactor.
- the concentration of molecular oxygen in the enzymatic reaction is from about 4 mg/L to about 14 mg/L.
- Another exemplary enzyme is a lichenase, which may be selected from the GH5, GH7, GH8, GH9, GH12, GH16, GH17, or GH26 families, preferably a GH16 enzyme, more preferably a GH16 enzyme derived from Bacillus subtilis (SEQ ID NO:2).
- the enzyme may be able to act on, for example, mixed-linkage glucans, which are glucans comprising a mixture of b-1,3 and b- 1,4 linkages, and may cleave them at b-1,4 glycosidic bonds.
- the b-glucans produced may fall largely within the size range of from 3 to about 7 residues, so they are particularly useful in the food, cosmetics, and nutraceutical industries.
- Mixed-linkage glucans are abundant in members of the grass and horsetail families, and as such, grass-based feedstocks such as straw have high levels of mixed- linkage glucans and may be acted upon usefully with lichenases.
- Preferred lichenases include GH5 lichenase from Bacillus subtilis (SEQ ID NO:2).
- Another alternative enzyme is a xylanase, which may act on, for example, feedstocks comprising a xylan backbone.
- the xylanase may be, for example, a glucuronoxylanase, an arabinoxylanase, or a glucuronoarabinoxylanase.
- the enzyme may be active on a variety of polymers having a xylan backbone, such as glucuronoxylan, arabinoxylan, and glucuronoarabinoxylan.
- both hardwood and softwood may comprise appropriate polysaccharides, with hardwood often comprising glucuronoxylan and softwood often comprising arabinoglucuronoxylan.
- Preferred xylanases include GH5 xylanases from Ruminiclostridium thermocellum (SEQ ID NOG) and Gonapodya prolifera (SEQ ID NO:4), and GH30 xylanases from Dickeya chrysanthemi (SEQ ID NOG), Bacillus subtilis (SEQ ID NO:6) and Bacteroides ovatus (SEQ ID NOG) and Trichoderma reesei (SEQ ID NO:l5 and 16).
- a mannanase which may act on, for example, feedstocks comprising a mannan backbone.
- the mannanase may be, for example, a mannanase, an glucomannanase, a galactomannanase or a galactoglucomannanase.
- the enzyme may be active on a variety of polymers having a mannan backbone, such as mannan, glucomannan, galactomannan or galactoglucomannan. These polymers are abundant in various plant-derived feedstocks, for example both hardwood and softwood may comprise appropriate polysaccharides.
- Preferred mannanases include GH5 mannanases from Trichoderma reesei (SEQ ID NO: 17) and Aspergillus niger (SEQ ID NO: 19) and a GH26 mannanase from Aspergillus niger (SEQ ID NO:l8).
- xyloglucanases and xyloglucan endoglucanases (XEGs), which are produced by numerous organisms, including plant-pathogenic microbes.
- Xyloglucanases and XEGs may be able to act on xyloglucan, a hemicellulosic b-1,4 glucan chain abundant in the primary cell wall of higher plants, which is decorated with xylose, some of the xylose residues being further decorated with other residues, such as galactose.
- the products may comprise xyloglucan oligosaccharides having a main chain of a length useful in the foodstuff, cosmetics, and nutraceutical industries.
- Preferred xyloglucanases include is a GH5 xyloglucanase from Bacteroides ovatus (SEQ ID NO: 8), and a GH74 xyloglucanase from Trichoderma reesei (SEQ ID NO:9).
- Enzymes used in such enzymatic reactions may have a sequence which has at least 70%, 75%, 80%, 85%, 90%, 95%, or 100% identity to a sequence of SEQ ID Nos: 1-25. Enzymes used herein may be functional equivalents of enzymes described herein or functional equivalents of SEQ ID Nos: 1-25.
- the enzymatic reaction may take place in solution and/or suspension or in a suitable reaction vessel. At a temperature or temperature protocol appropriate for the particular combination of enzyme and feedstock, the reaction may be allowed to progress for a certain amount of time (e.g., a predetermined amount of time), until the products have reached a desired concentration, or until some other requirement has been met.
- a certain amount of time e.g., a predetermined amount of time
- “suspension” refers to a composition comprising at least two immiscible phases, for example, a solid and a liquid phase, wherein the weight of the solid phase may be, as a percentage of the weight of the composition, in the range of from 0.5% to 30%, preferably from 1% to 20%, more preferably from 2% to 15%, yet more preferably from 3% to 10%.
- the suspension may comprise a suitable solvent, which is preferably water.
- the reaction mixture may be agitated, either constantly or at intervals.
- the agitation may take the form of (i) rhythmically moving the entire reaction vessel, (ii) a fan or other stirring device, (iii) a bubble spurging, or any other suitable method of agitation.
- the enzymatic reaction may be a microbial fermentation.
- the temperature and reaction time may be suitable for the growth of the microbial organism used.
- the microbial organism may be genetically altered to produce an enzyme suitable for the production of an oligosaccharide composition.
- the microbe may be, for example, a bacterium, for example Escherichia coli, or a fungus, such as Saccharomyces cerevisiae or Trichoderma reesei.
- an expression vector suitable for modifying the subject microorganism may be used such that it produces an enzyme or mixture of enzymes as described elsewhere herein.
- the expression vector which may be a plasmid or any other nucleic acid able to induce production of the enzyme, may comprise one or more of the following regulatory sequences so as to control the expression of the exogenous enzyme: regulatory sequences of a heat shock gene, regulatory sequences of a toxicity gene, regulatory sequences of a spore formation gene, or any other suitable regulatory sequence.
- the enzymatic reaction can be carried out at a temperature or temperature protocol appropriate to the enzymes and substrates used.
- the enzymatic reaction may be carried out at a constant temperature in the range of from 10 °C to 100 °C, preferably from 20 °C to 80 °C, more preferably from 40 °C to 60 °C.
- the temperature may be appropriate for such, for example, the enzymatic reaction may comprise the growth of E. coli and/or the temperature may be substantially constant and about 37 °C.
- the pH of the solution or suspension may affect the activity of the enzymes. Control of pH may aid in assuring that an enzymatic reaction proceeds at a suitable rate.
- the enzymatic reaction may take place at a pH in the range of from 2 to 10, preferably 3 to 8, more preferably 4 to 6.
- the enzymatic reaction may be allowed to continue for a certain time period before optionally being quenched and the products isolated or otherwise collected. This time period may be from 1 minute to 6 days, and is preferably from 0.5 days to 5 days, more preferably from 16 hours to 96 hours. The reaction may alternatively be allowed to proceed until no further catalysis occurs.
- the one or more feedstocks added to the enzymatic reaction may comprise polysaccharides.
- Such polysaccharides may have been produced by a separate reaction proceeding simultaneously or substantially simultaneously in the reaction vessel.
- the polysaccharides present in the enzymatic reaction may be partially cleaved by enzymes into useful oligosaccharides, leaving partially cleaved or uncleaved polysaccharides, which may include, but are not limited to, cellulose, xylan (such as glucuronoxylan, arabinoxylan, or glucuronoarabinoxylan), mannan (such as glucomannan, galactomannan, or galactoglucomannan), mixed-linkage glucan, xyloglucan chitin, chitosan, or lignocellulose.
- xylan such as glucuronoxylan, arabinoxylan, or glucuronoarabinoxylan
- mannan such as glucomannan, galactomannan,
- the enzymatic reaction may be allowed to continue to run until there is from 5% to 75% undigested polysaccharide-containing feedstocks remaining, preferably 5% to 70%, preferably 5% to 65%, more preferably 5% to 55%, or more preferably 10% to 50%.
- This can be monitored or checked by reducing end assays, such as the anthrone assay and/or by chromatographic methods such as thin-layer chromatography and/or high-performance anion exchange chromatography.
- Feedstocks suitable for producing the oligosaccharide profile may comprise, for example, cellulose, lignocellulose, chitin, chitosan, xylan (such as glucuronoxylan, arabinoxylan, and glucuronoarabinoxylan) and/or mannan (such as glucomannan, galactomannan, or galactoglucomannan), however, any feedstock which can be suitably acted upon is envisaged.
- the feedstocks comprise sugar cane, com stover, com cob, wheat bran, wheat straw, hardwood, or softwood.
- the feedstocks comprising such polysaccharides are also not particularly limited, as most plant matter is rich in such polymers.
- the feedstock may comprise plant biomass such as grain, grain chaff, bean pods, seed coats, and/or other seed materials; seaweeds; com stover, straw, bagasse, miscanthus, sorghum residue, switch grass, bamboo, and/or other monocotyledonous tissue; water hyacinth, leaf tissue, roots, and/or other vegetative matter; hardwood, hardwood chips, hardwood pulp, softwood, softwood chips, softwood pulp, paper, paper pulp, cardboard, and/or other wood-based feedstocks; crab shells, squid biomass, shrimp shells, and/or other marine biomass, and/or any combination of appropriate feedstocks.
- the feedstock comprises wheat straw or wood.
- any given natural feedstock is likely to comprise a mixture of different polysaccharides, it will sometimes be the case that a mixture of different enzymes is beneficial.
- Such a mixture may comprise one or more of any other enzyme.
- such a mixture might comprise an LPMO with an endo-glucanase, a xylanase with a lichenase, a cellobiohydrolase with a mannanase, or an endo-glucanase with a cellobiohydrolase, in which the enzyme partners are present in molar ratios preferably from 1 :100 to 100:1.
- pre-treatment of the feedstock is envisaged.
- pre -treatment is any process which makes a feedstock more easily acted upon by the enzymes inherent in the enzymatic reaction step.
- the pre-treatment can occur before the enzymatic reaction, and may comprise acid treatment by, for example, sulphuric acid, phosphoric acid, or trifluoroacetic acid; alkali treatment by, for example, potassium hydroxide, sodium hydroxide, or ammonia fibre expansion; heat treatment by, for example, hot water, hot steam, or hot acid; ionic liquid treatment, and related technologies; Alcell pulping, and related technologies; supercritical solvent, such as supercritical water treatment; and/or enzyme treatment by, for example, a hydrolase, lyase, or LPMO, or any mixture of the above processes.
- the one or more oligosaccharides and the one or more polysaccharides from the enzymatic reaction mixture are separated. This process can be performed in a variety of ways depending on the composition of the biomass used and the specificity of the enzymes used. As the reaction mixture will often comprise a mixture of soluble oligosaccharides and insoluble polysaccharides, the reaction mixture may be filtered to remove insoluble matter and prepare the soluble oligosaccharide obtained for further processing.
- the oligosaccharides may also be separated from the polysaccharides in a number of ways. They may be isolated based on solubility, so that a composition of soluble saccharides only is extracted for further processing, and/or isolated chromatographically to produce a composition with a narrower band of oligosaccharide chain lengths. Isolation may, for example, be based on precipitation, size-exclusion chromatography, ion-exchange chromatography, or filtration, ultrafiltration, or nanofiltration. In the case that isolation based on solubility is carried out, the profile of saccharides present in the isolated composition will depend on the original enzymatic reaction, as different polysaccharides decrease in solubility with length at different rates.
- oligosaccharides may be further treated to produce further products before incorporation into a foodstuff, cosmetic, or nutraceutical.
- This further treatment may comprise any chemical, physical, or enzymatic step, such as reduction, preferably reductive amination where appropriate; oxidation, caramelisation, modification with a Schiff base, or via the Maillard reaction, or by any combination of such steps, and may provide different products having properties which are improved for the desired purpose.
- the caramelisation properties, calorific value, flavour, and colour may be modified.
- the oligosaccharides may also be purified, for example, through precipitation, size-exclusion chromatography, ion-exchange chromatography, or filtration, ultrafiltration, or nanofiltration.
- polysaccharides may also be purified, for example, through precipitation, size-exclusion chromatography, ion-exchange chromatography, or filtration, ultrafiltration, or nanofiltration.
- ah or part of the fractions are then recombined at a ratio of from 1 :100 to 1 :1 polysaccharide:oligosaccharide, preferably from 1 :10 to 1 :1, preferably from 1 :90 to 1 :2, preferably from 1 :80 to 1 :3, preferably from 1 :70 to 1 :4, or preferably from 1 :60 to 1 :5.
- the specific ratio may depend on the desired properties of the final ingredient as well as the modifications and purifications that have been applied to the fractions.
- composition that can be generated by recombination of oligosaccharides is shown in Figure 1.
- the composition can have one or more oligosaccharides, wherein each type of oligosaccharide may have oligosaccharides with varying degrees of polymerization.
- the fractions can be recombined in a variety of ways, for example, by mixing a solution comprising ah or part of the oligosaccharide fraction and a solution and/or suspension comprising ah or part of the polysaccharide fraction, which may further be spray-dried, lyophilised, or condensed in some other way.
- the fractions may also be recombined by mixing a dry form comprising ah or part of the oligosaccharide fraction produced by spray-drying, lyophilisation, or condensation in some other way, with a dry form comprising ah or part of the polysaccharide fraction, produced by spray-drying, lyophilisation, or condensation in some other way.
- the oligosaccharide components of the final composition may comprise one or more of any type of oligosaccharide.
- they comprise cello-oligosaccharides, xylo- oligosaccharides, mixed-linkage glucan oligosaccharides, manno-oligosaccharides, xyloglucan oligosaccharides or chito-oligosaccharides, or derivatives of any of the aforementioned oligosaccharides.
- any such dry or liquid composition may be deemed an ingredient suitable for incorporation into a foodstuff, cosmetic, or nutraceutical at any stage of this process.
- dry compositions may be formed by well-known methods in the art such as spray-drying and/or lyophilisation.
- the dry compositions can be dissolved into a solution of various liquids including water, syrups, pastes, solvents, alcohols, etc. to form the liquid composition ingredient suitable for incorporation into a foodstuff, cosmetic, or nutraceutical.
- Liquid compositions may be particularly useful in foods that require a smooth texture such as candy, chocolate, and yoghurts.
- all or part of the fractions may then be recombined at a ratio of from 1 :100 to 1 :1 polysaccharide:oligosaccharide, preferably from 1 :10 to 1 :1, preferably from 1 :90 to 1 :2, preferably from 1 :80 to 1 :3, preferably from 1 :70 to 1 :4, or preferably from 1 :60 to 1 :5.
- the specific ratio may depend on the desired properties of the final ingredient as well as the modifications and purifications that have been applied to the fractions.
- compositions of the oligosaccharide products suitable for the application being considered are obtained, and further treatment and/or isolation is optionally carried out, the derivation of a foodstuff, cosmetic, or nutraceutical from the composition can furnish a very broad array of potential uses.
- the ingredients as described herein, can be useful in applications in which oligosaccharides, sugar, bulking sweeteners, low-intensity sweeteners, or other related food ingredients are conventionally used.
- a method for producing a foodstuff, cosmetic, or nutraceutical ingredient is described.
- the ingredient may comprise one or more oligosaccharides and one or more polysaccharides.
- the method may comprise the steps of:
- a) forming the one or more oligosaccharides and the one or more polysaccharides by an enzymatic reaction comprising the step of contacting, in a solution or suspension, one or more polysaccharide-cleaving enzymes and one or more feedstocks, wherein the one or more feedstocks comprise sugar cane, sugar cane bagasse, com stover, com cob, wheat bran, wheat straw, hardwood, softwood, cellulose, chitin, chitosan, xylan, xyloglucan, mixed-linkage glucan, mannan or lignocellulose;
- the one or more oligosaccharides may comprise cello-oligosaccharides, xylo- oligosaccharides, mixed-linkage glucan oligosaccharides, manno-oligosaccharides, xyloglucan oligosaccharides or chito-oligosaccharides, or derivatives of any of the aforementioned oligosaccharides.
- the polysaccharide-cleaving enzymes may be one of cellulase, xylanase, xyloglucanase, endo-glucanase, cellobiohydrolase, mannanase, lichenase or a lytic polysaccharide monooxygenase (LPMO), preferably selected from the group consisting of AA9, AA10, AA11, AA13, AA14 and AA15.
- the polysaccharide-cleaving enzyme may be prepared from T. reesei fungi and/or the enzymatic reaction runs until there is 5-75% undigested polysaccharide- containing feedstocks remaining, preferably 5-65%, more preferably 5-50%.
- the one or more polysaccharides may comprise cellulose, xylan, mannan, mixed-linkage glucan, chitin, chitosan or lignocellulose.
- the polysaccharide-containing feedstock may be pre- treated by acid, alkali, heat, pressure, and/or enzyme treatment.
- the polysaccharide-cleaving enzyme(s) may be operably linked to a catalytic or non-catalytic module, preferably wherein the polysaccharide-cleaving enzyme may be operably linked to a non-catalytic module and the non- catalytic module is a carbohydrate-binding module.
- the one or more oligosaccharides and one or more polysaccharides may be: purified; and/or undergo chemical, physical, or enzymatic treatment, such as reduction, oxidation, caramelisation, or Maillard reaction; and/or may be recombined by combining a spray- dried powder of oligosaccharides with a dried polysaccharide powder.
- the ingredient comprises three or more oligosaccharides of different molecular weights
- the method may comprise forming the three or more oligosaccharides by an enzymatic reaction, said enzymatic reaction comprising the step of contacting, in a solution or suspension, one or more polysaccharide-cleaving enzymes and one or more feedstocks.
- the polysaccharide-containing feedstock may comprise plant biomass, preferably sugar cane, com stover, com cob, wheat bran, wheat straw, hardwood, softwood, cellulose, chitin, chitosan, xylan, xyloglucan, mixed-linkage glucan, mannan or lignocellulose.
- plant biomass preferably sugar cane, com stover, com cob, wheat bran, wheat straw, hardwood, softwood, cellulose, chitin, chitosan, xylan, xyloglucan, mixed-linkage glucan, mannan or lignocellulose.
- At least one of the polysaccharide-cleaving enzymes may comprise one of cellulase, xylanase, xyloglucanase, endo-glucanase, cellobiohydrolase, mannanase, lichenase or a lytic polysaccharide monooxygenase (LPMO) and the polysaccharide-cleaving enzyme may be prepared from T. reesei fungi.
- LPMO lytic polysaccharide monooxygenase
- the composition may comprise monosaccharides at ⁇ 5% w/w of total oligosaccharide component (comprising glucose, xylose and/or mannose), disaccharides at >20% w/w of total oligosaccharide component (comprising cello-, xylo- and/or manno-oligosaccharides), trisaccharides at >5% w/w of total oligosaccharide component (comprising cello-, xylo- and/or manno-oligosaccharides) and tetrasaccharides at >2% w/w of total oligosaccharide component (comprising cello-, xylo- and/or manno-oligosaccharides).
- monosaccharides at ⁇ 5% w/w of total oligosaccharide component comprising glucose, xylose and/or mannose
- disaccharides at >20% w/w of
- the polysaccharide-containing feedstock may be pre-treated by acid, alkali, heat, pressure, and/or enzyme treatment.
- the polysaccharide-cleaving enzyme(s) may be operably linked to a catalytic or non-catalytic module, preferably wherein the polysaccharide-cleaving enzyme is operably linked to a non-catalytic module and the non-catalytic module is a carbohydrate-binding module.
- the oligosaccharides may be purified; and/or undergo chemical, physical, or enzymatic treatment, such as reduction, oxidation, caramelisation, or Maillard reaction; and/or are recombined by combining a spray-dried powder of oligosaccharides with a dried polysaccharide powder.
- Example 1 Improved dissolution of a cello-oligosaccharide and xylo-oligosaccharide combination composition.
- the xylo-oligosaccharide sample formed a clump that was difficult to mix into the blended strawberries, whereas the xylo-oligosaccharides and cellobiose mixture readily dispersed into the jam and did not form any clumps.
- Example 2 Improved dissolution of oligosaccharide combinations in water.
- Dissolution of xylo-oligosaccharides into water are improved when mixed with other oligosaccharides such as cello-oligosaccharide, manno-oligosaccharide, and mixed-linkage glucan oligosaccharides (MLGOs).
- MLGOs mixed-linkage glucan oligosaccharides
- 50 mg xylo-oligosaccharide powder was (a) left alone, or (b) mixed with 10 mg cellobiose, (c) mixed with 10 mg MLGOs or (d) mixed with 10 mg manno- oligosaccharides.
- oligosaccharide combinations and oligosaccharide-polysaccharide combinations perform better as sugar substitutes in cookies than individual oligosaccharides.
- Example 5 Improved solubility of cellobiose when combined with xylo-oligosaccharides
- Example 6 Modifying hygroscopicity of oligosaccharide powder by changing compositions
- compositions are to be used in a wide range of foodstuff, cosmetic, or nutraceutical applications, therefore the required hygroscopicity for each application can vary.
- the aim of this example was to test if hygroscopicity can be adapted by altering the oligosaccharide compositions.
- oligosaccharide compositions (cellobiose, 4:1 cellobiose:xylo-oligosaccharide, 3:2 cellobiose:xylo-oligosaccharide, 2:3 cellobiose:xylo-oligosaccharide, 1 :4 cellobiose:xylo-oligosaccharide, xylo-oligosaccharide) were incubated for 10 hours at 25 °C in 100% humidity.
- Example 7 Baked goods made using undigested polymeric cellulose
- Undigested polymeric cellulose from hydrolase reaction can perform functionally in cakes as well as untreated polymeric cellulose
- microcrystalline cellulose was incubated for 36 hours at 37 °C in 400 mL solution containing 2 mg GH7 cellobiohydrolase I ( Trichoderma longibrachiatum ), 5 mg GH12 cellulase (. Aspergillus nige r), and 0.3 mg GH6 cellobiohydrolase II (microbial) (all purchased from Megazyme, Ireland) with constant agitation at 800 rpm.
- GH7 cellobiohydrolase I Trichoderma longibrachiatum
- GH12 cellulase Aspergillus nige r
- GH6 cellobiohydrolase II microbial
- the oligosaccharide profile was analysed by thin-layer chromatography showing 41 % breakdown of polymeric cellulose into cello- oligosaccharides comprising mainly cellobiose with some cellotriose, cellotetraose, and glucose (shown in Figure 6).
- the cello-oligosaccharide mixture was separated from the undigested cellulose through filtration and both were dried.
- the undigested cellulose from the reaction was heated at 100 °C for 1 hour in 1M NaOH before being washed with water until neutral and dried.
- the two samples were whipped with 4 g unsalted butter, before mixing in 4 g egg, and then 4 g flour.
- Example 8 Baked goods made using undigested polymeric lignocellulose
- Undigested polymeric lignocellulose from partial cleavage of com cob can be added to cake mix without decrease in cake properties.
- the slurry was then incubated for 36 hours at 37 °C in 400 ml solution containing 1.6 ml T. reesei cellulase extract.
- oligosaccharide profile was analysed by thin-layer chromatography showing 68% breakdown of polymeric lignocellulose into oligosaccharide comprising mainly cellobiose with some xylose and glucose.
- the oligosaccharide mixture was separated from the undigested lignocellulose through filtration and dried.
- Example 9 Baked goods with undigested polymeric lignocellulose from partial cleavage of mahogany wood, wheat bran, and poplar wood.
- the mahogany slurry was incubated for 36 hours at 37 °C in 400 ml solution containing 1.6 ml T. reesei cellulase extract and 2 mg GH26 Mannanase ( Cellvibrio japonicas purchased from Megazyme, Ireland).
- the wheat bran slurry was incubated for 36 hours at 37 °C in 400 mL solution containing 1.6 ml T. reesei cellulase extract.
- the poplar slurry was incubated for 36 hours at 37 °C in 400 mL solution containing 2 mg GH7 cellobiohydrolase I ( Trichoderma longibrachiatum ), 5 mg GH12 cellulase (. Aspergillus niger ), 0.3 mg GH6 cellobiohydrolase II (microbial) (all purchased from Megazyme, Ireland), 10 mg Aspergillus oryzae xylanase (purchased from Sigma).
- oligosaccharide profile was analysed by thin-layer chromatography showing 68% breakdown of polymeric lignocellulose into oligosaccharide comprising mainly cellobiose with some xylose and glucose.
- the oligosaccharide mixture was separated from the undigested lignocellulose through filtration and dried.
- compositions are to be used in a wide range of foodstuffs, ideally up to levels comparable to sugar consumption in the average Western diet ( ⁇ 80 g/day). It is known that, at these levels, oligosaccharides, such as xylo-oligosaccharides, can cause gastrointestinal distress, including diarrhoea, discomfort, and bloating. For xylo-oligosaccharides the highest tolerated dose is 12 g/day. The aim of this example was to test if adding different polysaccharides to the oligosaccharide preparation before consumption would increase the gastrointestinal tolerance of the oligosaccharides, for example, by slowing gastric emptying, and enable far higher volumes to be comfortably consumed.
- each volunteer consumed an average of 30 g test oligosaccharides comprising cellobiose and xylo-oligosaccharides at ratios from 0:1 to 4:1.
- the maximum consumed on a single day was 50 g and the minimum was 20 g.
- each volunteer consumed an average of 70 g of test saccharides comprising cellobiose and xylo-oligosaccharides at ratios from 0:1 to 4:1, supplemented with microcrystalline cellulose or carboxymethylcellulose at 5-33% of the total test saccharide.
- the maximum consumed on a single day was 110 g and the minimum was 40 g ⁇
- Sample 1 comprises 15% undigested biomass mixed with 45% xylo- oligosaccharide and 40% cellobiose w/w.
- Sample 2 comprises 50% xylo-oligosaccharide mixed with 50% cellobiose w/w.
- Sample 3 comprises 10% xylo-oligosaccharide mixed with 90% cellobiose w/w.
- Sample 4 comprises 90% xylo-oligosaccharide mixed with 10% cellobiose w/w.
- the TES-AC-097 (UKAS) method was used to measure the moisture content. In this method the sample was heated to 70 °C in a vacuum chamber overnight and the loss in weight was measured. The moisture content results are given in Table 1 below. Sample 1 had the highest moisture content whereas sample 3 had the lowest. Samples 2 and 4 had intermediate moisture content between these two extremes and had similar moisture content to each other. The effect of moisture on flowability of particles can vary depending on the nature of the material. When particles absorb water, they can become cohesive and flow properties can be adversely affected. The higher moisture content found in Sample 1 may provide improved characteristics such as binding, moistness, etc. in baked goods. Table 1. Moisture content of powders (TES-AC-097 (UKAS))
- Samples from Example 11 were used and colour images were captured using a DigiEye system (Verivide).
- This instrument comprises an imaging cabinet with controlled D65 lighting conditions and a camera. Diffuse lighting, a fixed magnification, and consistent presentation conditions were used for all images.
- Figure 9 shows colour calibrated DigiEye images for all samples. The results for the imaging show that Sample 1 has a different colour due to the presence of biomass as compared to oligosaccharide mixtures in samples 2, 3 and 4.
- a* Position along an axis from green to red (where positive a* values indicate redness and negative a* values indicate greenness) is as shown in FIG. 10A.
- b* Position along an axis from blue to yellow (where positive b* values indicate yellowness and negative b* values indicate blueness) is as shown in FIG. 10B.
- Sample 1 had the highest moisture content and absorbed moisture at a faster rate than sample 3 which is unexpected.
- the rate of moisture pick-up of sample 1 was similar to samples 2 and 4.
- sample 1 had formed some clumps.
- Samples 2 and 4 had intermediate moisture content between samples 1 and 3 and absorbed moisture from the atmosphere at a similar rate to each other up to 24 hours.
- Sample 4 absorbed more moisture between 24 and 48 hours compared with sample 2.
- Sample 3 did not show any clump formation but sample 4 had lost its particulate nature and formed a viscous liquid. It could therefore be described as deliquescent.
- the cohesion strength describes a powder’s internal flow resistance, which depends on the adhesive forces between the particles.
- the measurements for samples made in Example 11 were conducted with an Anton Paar MCR Rheometer MCR102 equipped with a Powder Cell, a powder fluidizer with mass-flow controller (Fluidization Set Scientific), and a two-blade stirrer.
- the cohesion strength is determined with the two-blade stirrer from the torque recorded during the measurement and a geometry-specific factor.
- the method consists of two steps. During the first interval, residual influences from previous powder handling are erased. This is known as the Pressure-Drop Method. This was achieved by fully fluidizing the sample for 60 seconds. During the second interval, a constant rotational speed of 8 rpm was set while the volumetric flow was zero.
- the cohesion strength S in Pa was calculated by using linear regression over the last 20 data points.
- Example 17 Cream cheese icing made using oligosaccharide mixtures
- Acceptable Cell 2 :XOS w/w ratio ranges for cream cheese icing include 50:50 to 20:80 with optimal being 30:70.
- Results are shown in Figure 15.
- Cell 2 When Cell 2 is used alone the structure of the meringue is dry, dull and brittle and as a result it is unable to hold a proper structure of meringue and function as meringue properly.
- XOS As Cell 2 is replaced by XOS in 10% increments the structure becomes increasingly better able to stick together.
- Cell 2 :XOS w/w ratios Between about 70:30 and about 10:90 Cell 2 :XOS w/w ratios the texture of the meringue composition is similar to that when using sugar and has a sturdy thick meringue consistency.
- Cell 2 :XOS w/w ratios are similar to that when using sugar and has a smooth, shiny surface that retains structure like it does when sugar is used. As the mixture approaches and reaches 100% XOS the texture becomes increasingly thin and the surface becomes shinier.
- Acceptable Cell 2 :XOS w/w ratio ranges for meringue include 70:30 to 10:90 with optimal being 30:70
- Example 19 Chocolate chip muffin/cupcakes made using oligosaccharide mixtures
- Results are shown in Figure 16.
- Cell 2 When Cell 2 is used alone the structure of the muffin is dry, dense, lumpy and readily crumbles and as a result it is unable to hold a proper structure of muffin and function as muffin properly.
- the surface browns unevenly and wrinkles far more and is far lumpier than with sugar.
- XOS As Cell 2 is replaced by XOS in 10% increments the structure becomes increasingly better able to stick together. Between about 90:10 and about 10:90
- Cell 2 :XOS w/w ratios the texture of the muffin compositions is similar to that when using sugar and has a soft, cakey, chewy consistency, is able to hold moisture better and has a more sugar like rise and colour. Between about 90:10 and about 10:90 Cell 2 :XOS w/w ratios the surface appearance of the muffin compositions is similar to that when using sugar: it browns more evenly and has a more cake-like wrinkling structure.
- Acceptable Cell 2 :XOS w/w ratio ranges for muffins/cupcakes include 90:10 to 10:90 with optimal being between 60:40 and 40:60.
- Results are shown in Figure 17.
- Cell 2 When Cell 2 is used alone the structure of the cookie is very dry and dense as Cell 2 does not incorporate well into the dough. As a result the composition is unable to hold a proper structure of a cookie.
- the surface When Cell 2 is used alone the surface is also too light-colored and does not brown enough.
- Cell 2 is replaced by XOS in 10% increments the structure becomes increasingly better able to stick together.
- Between about 30:70 and about 10:90 Cell 2 :XOS w/w ratios the texture of the cookie compositions is similar to that when using sugar and has a chewy, crumbly consistency.
- Cell 2 :XOS w/w ratios the surface appearance of the cookie compositions is similar to that when using sugar and has a cracked, wrinkled, evenly-browned surface that retains structure like it does when sugar is used. As the mixture approaches and reaches 100% XOS the surface becomes too dark and pitted, the shape is unevenly distributed and partly bums at the edges, and the texture becomes increasingly thick, lumpy and granular as the XOS fails to incorporate properly into the cookie and sometimes forms clumps that will not readily break apart.
- Acceptable Cell 2 :XOS w/w ratio ranges for cookies include about 30:70 to about 10:90 with optimal being between about 20:80 and about 10:90.
- Example 21 Jams made using oligosaccharide mixtures
- Results are shown in Figure 18. When Cell 2 is used alone the structure of the jam is dry, sandy, dull, dense and solid and so unable to hold a proper structure of jam and function as jam properly.
- Example 22 Ice cream made using oligosaccharide mixtures
- a recipe that can be used to make such products is as follows:
- Example 23 Chocolate made using oligosaccharide mixtures
- a recipe that can be used to make such products is as follows:
- a recipe that can be used to make such products is as follows:
- Example 25 Soft caramels made using oligosaccharide mixtures
- a recipe that can be used to make such products is as follows:
- Example 26 Marshmallows made using oligosaccharide mixtures
- a recipe that can be used to make such products is as follows:
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| BR112021002910-9A BR112021002910A2 (en) | 2018-08-15 | 2019-08-16 | new compositions, their use and methods for their formation |
| MX2021001716A MX2021001716A (en) | 2018-08-15 | 2019-08-16 | Novel compositions, their use, and methods for their formation. |
| CN202410666863.6A CN118633720A (en) | 2018-08-15 | 2019-08-16 | Novel composition, use thereof and method of forming same |
| CA3109239A CA3109239A1 (en) | 2018-08-15 | 2019-08-16 | Novel compositions, their use, and methods for their formation |
| EP19758365.1A EP3836802A1 (en) | 2018-08-15 | 2019-08-16 | Novel compositions, their use, and methods for their formation |
| JP2021507671A JP7374991B2 (en) | 2018-08-15 | 2019-08-16 | Novel compositions, their uses, and methods of forming them |
| AU2019321182A AU2019321182B2 (en) | 2018-08-15 | 2019-08-16 | Novel compositions, their use, and methods for their formation |
| CN201980068017.1A CN113163828B (en) | 2018-08-15 | 2019-08-16 | Novel compositions, uses thereof and methods of forming the same |
| US16/844,960 US11006658B2 (en) | 2018-08-15 | 2020-04-09 | Compositions, their use, and methods for their formation |
| IL280809A IL280809B (en) | 2018-08-15 | 2021-02-11 | New preparations, their use and methods of their creation |
| US17/229,628 US11903399B2 (en) | 2018-08-15 | 2021-04-13 | Compositions, their use, and methods for their formation |
| US17/571,199 US11596165B2 (en) | 2018-08-15 | 2022-01-07 | Compositions, their use, and methods for their formation |
| US18/465,833 US12239152B2 (en) | 2018-08-15 | 2023-09-12 | Compositions, their use, and methods for their formation |
| US18/904,943 US20250151765A1 (en) | 2018-08-15 | 2024-10-02 | Novel compositions, their use, and methods for their formation |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021032647A1 (en) * | 2019-08-16 | 2021-02-25 | Cambridge Glycoscience Ltd | Methods of treating biomass to produce oligosaccharides and related compositions |
| US11006658B2 (en) | 2018-08-15 | 2021-05-18 | Cambridge Glycoscience Ltd | Compositions, their use, and methods for their formation |
| US11248247B2 (en) | 2018-02-21 | 2022-02-15 | Cambridge Glycoscience Ltd | Methods and systems of producing oligosaccharides |
| WO2022233885A3 (en) * | 2021-05-03 | 2022-12-08 | Cambridge Glycoscience Ltd | Soluble and insoluble saccharide compositions and related methods |
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| US11248247B2 (en) | 2018-02-21 | 2022-02-15 | Cambridge Glycoscience Ltd | Methods and systems of producing oligosaccharides |
| US11006658B2 (en) | 2018-08-15 | 2021-05-18 | Cambridge Glycoscience Ltd | Compositions, their use, and methods for their formation |
| US11596165B2 (en) | 2018-08-15 | 2023-03-07 | Cambridge Glycoscience Ltd | Compositions, their use, and methods for their formation |
| US11903399B2 (en) | 2018-08-15 | 2024-02-20 | Cambridge Glycoscience Ltd | Compositions, their use, and methods for their formation |
| US12239152B2 (en) | 2018-08-15 | 2025-03-04 | Cambridge Glycoscience Ltd | Compositions, their use, and methods for their formation |
| WO2021032647A1 (en) * | 2019-08-16 | 2021-02-25 | Cambridge Glycoscience Ltd | Methods of treating biomass to produce oligosaccharides and related compositions |
| US11297865B2 (en) | 2019-08-16 | 2022-04-12 | Cambridge Glycoscience Ltd | Methods of treating biomass to produce oligosaccharides and related compositions |
| US11771123B2 (en) | 2019-08-16 | 2023-10-03 | Cambridge Glycoscience Ltd | Methods for treating biomass to produce oligosaccharides and related compositions |
| US11871763B2 (en) | 2019-12-12 | 2024-01-16 | Cambridge Glycoscience Ltd | Low sugar multiphase foodstuffs |
| US20230276801A1 (en) * | 2020-07-27 | 2023-09-07 | Universidad Politecnica De Madrid | Methods and compositions to improve plant health and protection |
| WO2022233885A3 (en) * | 2021-05-03 | 2022-12-08 | Cambridge Glycoscience Ltd | Soluble and insoluble saccharide compositions and related methods |
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Also Published As
| Publication number | Publication date |
|---|---|
| US20250151765A1 (en) | 2025-05-15 |
| CA3109239A1 (en) | 2020-02-20 |
| MX2021001716A (en) | 2021-05-31 |
| EP3836802A1 (en) | 2021-06-23 |
| US20220132897A1 (en) | 2022-05-05 |
| US11596165B2 (en) | 2023-03-07 |
| JP7374991B2 (en) | 2023-11-07 |
| IL280809B (en) | 2022-05-01 |
| US20240180216A1 (en) | 2024-06-06 |
| US20210315245A1 (en) | 2021-10-14 |
| BR112021002910A2 (en) | 2021-07-20 |
| US11903399B2 (en) | 2024-02-20 |
| AU2019321182A1 (en) | 2021-03-11 |
| CN113163828A (en) | 2021-07-23 |
| IL280809A (en) | 2021-04-29 |
| JP2021536227A (en) | 2021-12-27 |
| US20200352203A1 (en) | 2020-11-12 |
| AU2019321182B2 (en) | 2025-01-09 |
| US11006658B2 (en) | 2021-05-18 |
| CN113163828B (en) | 2024-04-26 |
| CN118633720A (en) | 2024-09-13 |
| US12239152B2 (en) | 2025-03-04 |
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